Heterocyclic compound, light-emitting device including the heterocyclic compound, and electronic apparatus including the light-emitting device

ABSTRACT

Provided are a heterocyclic compound represented by Formula 1, an organic light-emitting device including the heterocyclic compound, and an electronic apparatus including the light-emitting device. The light-emitting device includes: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode, and including an emission layer.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2020-0147087, filed on Nov. 5, 2020, in the KoreanIntellectual Property Office, the entire content of which is herebyincorporated by reference.

BACKGROUND 1. Field

One or more embodiments of the present disclosure relate to aheterocyclic compound, a light-emitting device including theheterocyclic compound, and an electronic apparatus including thelight-emitting device.

2. Description of Related Art

From among light-emitting devices, organic light-emitting devices(OLEDs) are self-emission devices that, as compared with other devices,have wide viewing angles, high contrast ratios, short response times,and excellent characteristics in terms of luminance, driving voltage,and response speed, and produce full-color images.

OLEDs may include a first electrode located on a substrate, and a holetransport region, an emission layer, an electron transport region, and asecond electrode sequentially stacked on the first electrode. Holesprovided from the first electrode may move toward the emission layerthrough the hole transport region, and electrons provided from thesecond electrode may move toward the emission layer through the electrontransport region. Carriers, such as holes and electrons, recombine inthe emission layer to produce excitons. These excitons transition froman excited state to a ground state to thereby generate light.

SUMMARY

One or more embodiments of the present disclosure relate to aheterocyclic compound, a light-emitting device including theheterocyclic compound, and an electronic apparatus including thelight-emitting device.

Additional aspects of embodiments will be set forth in part in thedescription which follows and, in part, will be apparent from thedescription, or may be learned by practice of the presented embodimentsof the disclosure.

According to one or more embodiments, a heterocyclic compound may berepresented by Formula 1.

In Formula 1,

X₁ may be O, S, or Si(R₁₁)(R₁₂),

Ar may be a C₅-C₆₀ carbocyclic group or a C₁-C₆₀ heterocyclic group,

A₁ may be a C₃-C₆₀ carbocyclic group unsubstituted or substituted withat least one R₁₀ or a C₁-C₆₀ heterocyclic group unsubstituted orsubstituted with at least one R₁₀,

L₁ may be a single bond, a C₅-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R_(10a), or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a),

n1 may be an integer selected from 1 to 3,

R₁ to R₃, R₁₀, R₁₁, and R₁₂ may each independently be hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a C₁-C₆₀ alkyl group unsubstituted or substituted with at leastone R_(10a), a C₂-C₆₀ alkenyl group unsubstituted or substituted with atleast one R_(10a), a C₂-C₆₀ alkynyl group unsubstituted or substitutedwith at least one R_(10a), a C₁-C₆₀ alkoxy group unsubstituted orsubstituted with at least one R_(10a), a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a), a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a), a C₆-C₆₀ aryloxy group unsubstituted or substituted with atleast one R_(10a), a C₆-C₆₀ arylthio group unsubstituted or substitutedwith at least one R_(10a), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

d1 may be an integer selected from 1 to 8,

d2 may be an integer selected from 1 to 10,

d3 may be an integer selected from 1 to 7,

R_(10a) may be:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anamidino group, a hydrazino group, a hydrazono group, or a nitro group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, ora C₁-C₆₀ alkoxy group, each unsubstituted or substituted with deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, aC₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂),—B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or anycombination thereof,

a C₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀aryloxy group, or a C₆-C₆₀ arylthio group, each unsubstituted orsubstituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₆₀ carbocyclic group,a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthiogroup, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof, or

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂), or —P(Q₃₁)(Q₃₂),

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are eachindependently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, or a C₃-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group, each unsubstituted orsubstituted with deuterium, —F, a cyano group, a C₁-C₆₀ alkyl group, aC₁-C₆₀ alkoxy group, a phenyl group, a biphenyl group, or anycombination thereof.

According to another aspect of one or more embodiments, a light-emittingdevice may include a first electrode, a second electrode facing thefirst electrode, an interlayer between the first electrode and thesecond electrode and including an emission layer, and at least one ofthe heterocyclic compound represented by Formula 1.

According to another aspect of one or more embodiments, an electronicapparatus may include the light-emitting device, and further include athin-film transistor, wherein the thin-film transistor may include asource electrode and a drain electrode, and the first electrode of thelight-emitting device is electrically coupled to the source electrode orthe drain electrode.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other aspects and features of certain embodiments of thedisclosure will be more apparent from the following description taken inconjunction with the accompanying drawings, in which:

FIGS. 1 to 3 are each a schematic cross-sectional view of a structure ofa light-emitting device according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments, examples ofwhich are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present embodiments may have different forms and should not beconstrued as being limited to the descriptions set forth herein.Accordingly, the embodiments are merely described below, by referring tothe figures, to explain aspects of embodiments of the presentdescription. As used herein, the term “and/or” includes any and allcombinations of one or more of the associated listed items. Throughoutthe disclosure, the expression “at least one of a, b or c” indicatesonly a, only b, only c, both a and b, both a and c, both b and c, all ofa, b, and c, or variations thereof.

The heterocyclic compound may be represented by Formula 1 below.

In Formula 1,

X₁ may be O, S, or Si(R₁₁)(R₁₂).

Ar may be a C₅-C₆₀ carbocyclic group or a C₁-C₆₀ heterocyclic group.

In an embodiment, Ar may be a benzene group, a naphthalene group, ananthracene group, a phenanthrene group, a triphenylene group, a pyrenegroup, a chrysene group, a cyclopentadiene group, a1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group,an indole group, a benzoborole group, a benzophosphole group, an indenegroup, a benzosilole group, a benzogermole group, a benzothiophenegroup, a benzoselenophene group, a benzofuran group, a carbazole group,a dibenzoborole group, a dibenzophosphole group, a fluorene group, adibenzosilole group, a dibenzogermole group, a dibenzothiophene group, adibenzoselenophene group, a dibenzofuran group, a dibenzothiophene5-oxide group, 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxidegroup, a pyridine group, a pyrimidine group, a pyrazine group, apyridazine group, a triazine group, a quinoline group, an isoquinolinegroup, a quinoxaline group, a quinazoline group, a phenanthroline group,a pyrrole group, a pyrazole group, an imidazole group, a triazole group,an oxazole group, an isooxazole group, a thiazole group, an isothiazolegroup, an oxadiazole group, a thiadiazole group, a benzopyrazole group,a benzimidazole group, a benzoxazole group, a benzothiazole group, abenzoxadiazole group, a benzothiadiazole group, a5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinolinegroup.

A₁ may be a C₅-C₆₀ carbocyclic group unsubstituted or substituted withat least one R₁₀ or a C₁-C₆₀ heterocyclic group unsubstituted orsubstituted with at least one R₁₀.

In an embodiment, A₁ may be a π electron-rich C₃-C₆₀ cyclic groupunsubstituted or substituted with at least one R₁₀ or a πelectron-deficient nitrogen-containing C₁-C₆₀ cyclic group unsubstitutedor substituted with at least one R₁₀.

In some embodiments, the π electron-deficient nitrogen-containing C₁-C₆₀cyclic group may be a) a first ring, b) a condensed ring in which atleast two first rings are condensed (e.g., combined together with eachother), or c) a condensed ring in which at least one first ring and atleast one second ring are condensed (e.g., combined together with eachother),

the π electron-rich C₃-C₆₀ cyclic group may be a) second ring or b) acondensed ring in which at least two second rings are condensed (e.g.,combined together with each other),

the first ring may be an imidazole group, a pyrazole group, a thiazolegroup, an isothiazole group, an oxazole group, an isoxazole group, apyridine group, a pyrazine group, a pyridazine group, a pyrimidinegroup, a triazole group, a tetrazole group, an oxadiazole group, atriazine group, or a thiadiazole group, and

the second ring may be a benzene group, a cyclopentadiene group, apyrrole group, a furan group, a thiophene group, or a silole group.

In one or more embodiments, the π electron-deficient nitrogen-containingC₁-C₆₀ cyclic group may be an imidazole group, a pyrazole group, athiazole group, an isothiazole group, an oxazole group, an isoxazolegroup, a pyridine group, a pyrazine group, a pyridazine group, apyrimidine group, an indazole group, a purine group, a quinoline group,an isoquinoline group, a benzoquinoline group, a benzoisoquinolinegroup, a phthalazine group, a naphthyridine group, a quinoxaline group,a benzoquinoxaline group, a quinazoline group, a cinnoline group, aphenanthridine group, an acridine group, a phenanthroline group, aphenazine group, a benzimidazole group, an isobenzothiazole group, abenzoxazole group, a benzoisoxazole group, a triazole group, a tetrazolegroup, an oxadiazole group, a triazine group, a thiadiazole group, animidazopyridine group, an imidazopyrimidine group, an azacarbazolegroup, an azadibenzofuran group, an azadibenzothiophene group, anazadibenzosilole group, an acridine group, or a pyridopyrazine group,and

the π electron-rich C₃-C₆₀ cyclic group may be a benzene group, aheptalene group, an indene group, a naphthalene group, an azulene group,an indacene group, acenaphthylene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentacene group, a hexacene group, a pentaphene group, a rubicene group,a coronene group, an ovalene group, a pyrrole group, a furan group, athiophene group, an isoindole group, an indole group, an indene group, abenzofuran group, a benzothiophene group, a benzosilole group, anaphthopyrrole group, a naphthofuran group, a naphthothiophene group, anaphthosilole group, a benzocarbazole group, a dibenzocarbazole group, adibenzofuran group, a dibenzothiophene group, a carbazole group, adibenzosilole group, an indenocarbazole group, an indolocarbazole group,a benzofurocarbazole group, a benzothienocarbazole group, abenzosilolocarbazole group, a triindolobenzene group, apyrrolophenanthrene group, a furanophenanthrene group, athienophenanthrene group, a benzonaphthofuran group, abenzonaphthothiophene group, an (indolo)phenanthrene group, a(benzofuran)phenanthrene group, or a (benzothieno)phenanthrene group.

In an embodiment, A₁ may be a benzene group, a naphthalene group, ananthracene group, a phenanthrene group, a triphenylene group, a pyrenegroup, a chrysene group, cyclopentadiene group, a1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group,an indole group, a benzoborole group, a benzophosphole group, an indenegroup, a benzosilole group, a benzogermole group, a benzothiophenegroup, a benzoselenophene group, a benzofuran group, a carbazole group,a dibenzoborole group, a dibenzophosphole group, a fluorene group, adibenzosilole group, a dibenzogermole group, a dibenzothiophene group, adibenzoselenophene group, a dibenzofuran group, a dibenzothiophene5-oxide group, 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxidegroup, an azaindole group, an azabenzoborole group, an azabenzophospholegroup, an azaindene group, an azabenzosilole group, an azabenzogermolegroup, an azabenzothiophene group, an azabenzoselenophene group, anazabenzofuran group, an azacarbazole group, an azadibenzoborole group,an azadibenzophosphole group, an azafluorene group, an azadibenzosilolegroup, an azadibenzogermole group, an azadibenzothiophene group, anazadibenzoselenophene group, an azadibenzofuran group, anazadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, anazadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a pyrrole group, a pyrazolegroup, an imidazole group, a triazole group, an oxazole group, anisooxazole group, a thiazole group, an isothiazole group, an oxadiazolegroup, a thiadiazole group, a benzopyrazole group, a benzimidazolegroup, a benzoxazole group, a benzothiazole group, a benzoxadiazolegroup, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group,or a 5,6,7,8-tetrahydroquinoline group unsubstituted or substituted withat least one R₁₀.

R₁₀ is the same as described in the present specification.

In an embodiment, A₁ may be a group represented by Formula 2 or Formula3:

In Formulae 2 and 3,

Y₁ may be N or C(Ria),

Y₂ may be N or C(R_(2a)),

Y₃ may be N or C(R_(3a)),

L₂₁, L₂₂, and L₃₁ may each independently be a single bond, a C₅-C₆₀carbocyclic group unsubstituted or substituted with at least oneR_(10a), or a C₁-C₆₀ heterocyclic group unsubstituted or substitutedwith at least one R_(10a),

n21, n22, and n31 may each independently be an integer selected from 1to 3,

* indicates a binding site to a neighboring atom,

R_(1a) to R_(3a), R₂₁, R₂₂, R₃₁, and R₃₂ may each independently behydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, a C₁-C₆₀ alkyl group unsubstituted or substituted with atleast one R_(10a), a C₂-C₆₀ alkenyl group unsubstituted or substitutedwith at least one R_(10a), a C₂-C₆₀ alkynyl group unsubstituted orsubstituted with at least one R_(10a), a C₁-C₆₀ alkoxy groupunsubstituted or substituted with at least one R_(10a), a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least oneR_(10a), a C₁-C₆₀ heterocyclic group unsubstituted or substituted withat least one R_(10a), a C₆-C₆₀ aryloxy group unsubstituted orsubstituted with at least one R_(10a), a C₆-C₆₀ arylthio groupunsubstituted or substituted with at least one R_(10a), —Si(Q₁)(Q₂)(Q₃),—N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

d21, d22 and d31 are each independently an integer selected from 1 to10,

d32 is an integer selected from 1 to 7, and

R_(10a) is the same as described in the present specification. As usedherein, the term “single bond” may refer to a single covalent bond.

L₁ may be a single bond, a C₅-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R₁₀, or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a).

In an embodiment, L₁, L₂₁, L₂₂ and L₃₁ may each independently be: asingle bond; or

a benzene group, a naphthalene group, an anthracene group, aphenanthrene group, a triphenylene group, a pyrene group, a chrysenegroup, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, athiophene group, a furan group, an indole group, a benzoborole group, abenzophosphole group, an indene group, a benzosilole group, abenzogermole group, a benzothiophene group, a benzoselenophene group, abenzofuran group, a carbazole group, a dibenzoborole group, adibenzophosphole group, a fluorene group, a dibenzosilole group, adibenzogermole group, a dibenzothiophene group, a dibenzoselenophenegroup, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-afluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindolegroup, an azabenzoborole group, an azabenzophosphole group, an azaindenegroup, an azabenzosilole group, an azabenzogermole group, anazabenzothiophene group, an azabenzoselenophene group, an azabenzofurangroup, an azacarbazole group, an azadibenzoborole group, anazadibenzophosphole group, an azafluorene group, an azadibenzosilolegroup, an azadibenzogermole group, an azadibenzothiophene group, anazadibenzoselenophene group, an azadibenzofuran group, anazadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, anazadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a pyrrole group, a pyrazolegroup, an imidazole group, a triazole group, an oxazole group, anisooxazole group, a thiazole group, an isothiazole group, an oxadiazolegroup, a thiadiazole group, a benzopyrazole group, a benzimidazolegroup, a benzoxazole group, a benzothiazole group, a benzoxadiazolegroup, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group,or a 5,6,7,8-tetrahydroquinoline group, each unsubstituted orsubstituted with at least one R_(10a), and

R_(10a) is the same as described in the present specification.

In an embodiment, L₁, L₂₁, L₂₂ and L₃₁ may each independently be asingle bond, or

may be selected from Formulae 10-1 to 10-40,

In Formulae 10-1 to 10-40,

Y₁ is O or S,

Y₂ is O, S, N(Z₃), or C(Z₃)(Z₄),

Z₁ to Z₄ are each the same as described in connection with R₁ in thepresent specification,

e4 is an integer selected from 1 to 4,

e6 is an integer selected from 1 to 6,

e7 is an integer selected from 1 to 7,

e8 is an integer selected from 1 to 8, and

* and *′ each indicate a binding site to a neighboring atom.

n1 may be an integer selected from 1 to 3.

R₁ to R₃, R₁₀, R₁₁, and R₁₂ may each independently be hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a C₁-C₆₀ alkyl group unsubstituted or substituted with at leastone R_(10a), a C₂-C₆₀ alkenyl group unsubstituted or substituted with atleast one R_(10a), a C₂-C₆₀ alkynyl group unsubstituted or substitutedwith at least one R_(10a), a C₁-C₆₀ alkoxy group unsubstituted orsubstituted with at least one R_(10a), a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a), a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a), a C₆-C₆₀ aryloxy group unsubstituted or substituted with atleast one R_(10a), a C₆-C₆₀ arylthio group unsubstituted or substitutedwith at least one R_(10a), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂).

In Formula 1, d1 may be an integer selected from 1 to 8,

d2 may be an integer selected from 1 to 10, and

d3 may be an integer selected from 1 to 7.

R_(10a) may be:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or anitro group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, ora C₁-C₆₀ alkoxy group, each unsubstituted or substituted with deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, aC₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂),—B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or anycombination thereof;

a C₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀aryloxy group, or a C₆-C₆₀ arylthio group, each unsubstituted orsubstituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₆₀ carbocyclic group,a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthiogroup, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof; or

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂),

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may eachindependently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxylgroup; a cyano group; a nitro group; a C₁-C₆₀ alkyl group; a C₂-C₆₀alkenyl group; a C₂-C₆₀ alkynyl group; a C₁-C₆₀ alkoxy group; or aC₃-C₆₀ carbocyclic group or a C₁-C₆₀ heterocyclic group, eachunsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a biphenyl group, orany combination thereof.

In an embodiment, Formula 1 may be represented by Formula 1-1 below:

In Formula 1-1, X₁, A₁, L₁, n1, R₁ to R₃, and d1 to d3 are each the sameas described in the present specification. In one or more embodiments ofFormula 1-1, d2 may be an integer selected from 1 to 5.

In an embodiment, Formula 1 may be represented by one of Formulae 1-11to 1-14.

In Formulae 1-11 to 1-14, X₁, Ar, L₁, n1, A₁, R₁ to R₃, and d1 to d3 areeach the same as described in the present specification.

In an embodiment, Formula 1 may be represented by one of Formulae 1-21to 1-24.

In Formulae 1-21 to 1-24, X₁, Ar, L₁, n1, A₁, R₁ to R₃, and d1 to d3 areeach the same as described in the present specification. In one or moreembodiments of Formulae 1-21 to 1-24, d2 may be an integer selected from1 to 5.

In an embodiment, Formula 3 may be represented by one of Formulae 3-1 to3-4.

In Formulae 3-1 to 3-4, L₃₁, n31, R₃₁, R₃₂, d31, and d32 are each thesame as described in the present specification.

In an embodiment, R₁ to R₃, R₁₀ to R₁₂, R_(1a) to R_(3a), R₂₁, R₂₂, R₃₁,and R₃₂ may each independently be selected from: hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one of deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₁₀ alkyl group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, anda pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acycloctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, an azacarbazolyl group, anazadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenylgroup, and an azadibenzosilolyl group, each unsubstituted or substitutedwith at least one of deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂,—CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cycloctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a C₁-C₁₀ alkylphenyl group, a naphthyl group, a fluorenyl group,a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, an imidazopyrimidinyl group, anazacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenylgroup, an azafluorenyl group, an azadibenzosilolyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —P(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂); and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and—P(═O)(Q₁)(Q₂),

wherein Q₁ to Q₃, and Q₃₁ to Q₃₃ may each independently be selectedfrom:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃,—CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, and —CD₂CDH₂, and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, a naphthyl group, a pyridinyl group, a pyrimidinyl group, apyridazinyl group, a pyrazinyl group, and a triazinyl group, eachunsubstituted or substituted with at least one selected from deuterium,a C₁-C₁₀ alkyl group, a phenyl group, a biphenyl group, a pyridinylgroup, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, anda triazinyl group.

In one or more embodiments, R₁ to R₃, R₁₀ to R₁₂, R_(1a) to R_(3a), R₂₁,R₂₂, R₃₁, and R₃₂ may each independently be selected from:

hydrogen, deuterium, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group, each substituted withat least one selected from deuterium, —CD₃, —CD₂H, —CDH₂, C₁-C₁₀ alkylgroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a biphenyl group, and a naphthylgroup;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an isoindolyl group, an indolylgroup, an indazolyl group, a purinyl group, a carbazolyl group, abenzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, and adibenzocarbazolyl group, each unsubstituted or substituted with at leastone selected from deuterium, —CD₃, —CD₂H, —CDH₂, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a C₁-C₁₀ alkylphenyl group, a naphthyl group, a fluorenyl group,a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a carbazolyl group,a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂); and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), and —B(Q₁)(Q₂),

wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may each independently be selected from:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃,—CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, and —CD₂CDH₂, and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group, each unsubstituted or substituted with atleast one selected from deuterium, a C₁-C₁₀ alkyl group, a phenyl group,and a biphenyl group.

In an embodiment, the heterocyclic compound may be selected fromCompounds 1 to 130, but embodiments are not limited thereto:

The heterocyclic compound represented by Formula 1 has a core structurein which a triphenylsilyl group is connected to (bonded to) a carbazolering, and includes, as a substituent, a carbazole group or a triazinegroup.

Because Formula 1 has the core structure in which a triphenylsilyl groupis connected to (bonded to) a carbazole ring, and thus, luminescenceefficiency and energy transfer may be improved, and when fluorescent andphosphorescent dopants of the related art are combined therewith,efficiency and lifespan characteristics of a light-emitting device maybe improved.

For example, because the two phenyl groups of the triphenylsilyl groupin the core structure are connected with (bonded with) *—O—*, *—S—*′ or*—Si(R₁₁)(R₁₂)—*′, in the aspect of molecular binding energy (BDE),molecules (e.g., the heterocyclic compound represented by Formula 1) mayhave strong rigidity.

Also, because the heterocyclic compound includes, as a substituent, atleast one carbazole group or triazine group, the hole transportabilityor electron transportability of an emission layer may be improved,thereby resulting in the improvement of efficiency and lifespancharacteristics of a light-emitting device.

Therefore, a light-emitting device, for example, an organiclight-emitting device, including the heterocyclic compound representedby Formula 1 may have a low driving voltage, high maximum quantumefficiency, high efficiency, and long lifespan.

Methods of synthesizing the heterocyclic compound represented by Formula1 may be readily apparent to those of ordinary skill in the art byreferring to Examples described herein.

At least one heterocyclic compound represented by Formula 1 may be usedin a light-emitting device (for example, an organic light-emittingdevice).

In an embodiment, a light-emitting device may include a first electrode,a second electrode facing the first electrode, an interlayer locatedbetween the first electrode and the second electrode and including anemission layer, and at least one heterocyclic compound represented byFormula 1.

In one or more embodiments, the first electrode may be an anode, thesecond electrode may be a cathode, the interlayer may further include ahole transport region between the first electrode and the emission layerand an electron transport region between the emission layer and thesecond electrode, the hole transport region may include a hole injectionlayer, a hole transport layer, an emission auxiliary layer, an electronblocking layer, or any combination thereof, and the electron transportregion may include a hole blocking layer, an electron transport layer,an electron injection layer, or any combination thereof.

In an embodiment, the emission layer may include the heterocycliccompound.

In an embodiment, the emission layer may include a host and a dopant,

the host and the dopant may be different from each other,

the amount of the host may be greater than the amount of the dopant, and

the host may include the heterocyclic compound.

In an embodiment, the dopant may be a fluorescent dopant orphosphorescent dopant.

In an embodiment, the dopant may include a transition metal.

In an embodiment, the emission layer may emit blue light or blue-greenlight.

In an embodiment, the emission layer may emit blue light or blue-greenlight, each having a maximum emission wavelength range of about 400 nmto about 500 nm.

As used herein, the expression “(an interlayer) includes a heterocycliccompound” may be construed as meaning “(an interlayer) may include oneheterocyclic compound represented by Formula 1 or two or more differentheterocyclic compounds represented by Formula 1.”

In one or more embodiments, the interlayer may include only Compound 1as the heterocyclic compound. In this regard, Compound 1 may exist inthe emission layer of the light-emitting device. In some embodiments,the interlayer may include, as the heterocyclic compounds, Compounds 1and 2. In this regard, Compound 1 and Compound 2 may exist in anidentical layer (for example, Compound 1 and Compound 2 may all exist inan emission layer), or different layers (for example, Compound 1 mayexist in an emission layer and Compound 2 may exist in an electrontransport region).

The term “interlayer,” as used herein, refers to a single layer and/orall of a plurality of layers located between a first electrode and asecond electrode of a light-emitting device.

Another aspect of one or more embodiments provides an electronicapparatus including the light-emitting device. The electronic apparatusmay further include a thin-film transistor.

In one or more embodiments, the electronic apparatus may further includea thin-film transistor including a source electrode and a drainelectrode, and the first electrode of the light-emitting device may beelectrically coupled to the source electrode or the drain electrode.

In an embodiment, the electronic apparatus may further include a colorfilter, a color conversion layer, a touch screen layer, a polarizinglayer, or any combination thereof. In one or more embodiments, theelectronic apparatus may be a flat panel display apparatus, butembodiments of the present disclosure are not limited thereto.

Additional details of the electronic apparatus are the same as describedin the present specification.

Description of FIG. 1

FIG. 1 is a schematic cross-sectional view of a light-emitting device 10according to an embodiment. The light-emitting device 10 includes afirst electrode 110, an interlayer 130, and a second electrode 150.

Hereinafter, the structure of the light-emitting device 10 according toan embodiment and a method of manufacturing the light-emitting device 10will be described in connection with FIG. 1.

First Electrode 110

In FIG. 1, a substrate may be additionally located under the firstelectrode 110 or above the second electrode 150. As the substrate, aglass substrate and/or a plastic substrate may be used. In one or moreembodiments, the substrate may be a flexible substrate, and may includeplastics having excellent heat resistance and durability, such aspolyimide, polyethylene terephthalate (PET), polycarbonate, polyethylenenaphthalate, polyarylate (PAR), polyetherimide, or any combinationthereof.

The first electrode 110 may be formed by, for example, depositing and/orsputtering a material for forming the first electrode 110 on thesubstrate. When the first electrode 110 is an anode, a material forforming the first electrode 110 may be a high work function materialthat facilitates injection of holes.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, indium tin oxide (ITO),indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), or anycombination thereof may be used as a material for forming a firstelectrode. In one or more embodiments, when the first electrode 110 is asemi-transmissive electrode or a reflective electrode, magnesium (Mg),silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combinationthereof may be used as a material for forming a first electrode.

The first electrode 110 may have a single-layered structure including(e.g., consisting of) a single layer or a multi-layered structureincluding a plurality of layers. In one or more embodiments, the firstelectrode 110 may have a three-layered structure of ITO/Ag/ITO.

Interlayer 130

The interlayer 130 may be on the first electrode 110. The interlayer 130may include an emission layer.

The interlayer 130 may include the heterocyclic compound represented byFormula 1.

The interlayer 130 may further include a hole transport region betweenthe first electrode 110 and the emission layer and an electron transportregion between the emission layer and the second electrode 150.

The interlayer 130 may further include metal-containing compounds suchas organometallic compounds, inorganic materials such as quantum dots,and/or the like, in addition to various suitable organic materials.

In one or more embodiments, the interlayer 130 may include, i) two ormore emitting units sequentially stacked between the first electrode 110and the second electrode 150 and ii) a charge generation layer betweenthe two emitting units. When the interlayer 130 includes the emittingunit and the charge generation layer as described above, thelight-emitting device 10 may be a tandem light-emitting device.

Hole Transport Region in Interlayer 130

The hole transport region may have: i) a single-layered structureincluding (e.g., consisting of) a single layer including (e.g.,consisting of) a single material, ii) a single-layered structureincluding (e.g., consisting of) a single layer including (e.g.,consisting of) a plurality of different materials, or iii) amulti-layered structure including a plurality of layers includingdifferent materials.

The hole transport region may include a hole injection layer, a holetransport layer, an emission auxiliary layer, an electron blockinglayer, or any combination thereof.

For example, the hole transport region may have a multi-layeredstructure including a hole injection layer/hole transport layerstructure, a hole injection layer/hole transport layer/emissionauxiliary layer structure, a hole injection layer/emission auxiliarylayer structure, a hole transport layer/emission auxiliary layerstructure, or a hole injection layer/hole transport layer/electronblocking layer structure, wherein, in each structure, layers are stackedsequentially from the first electrode 110.

The hole transport region may include a compound represented by Formula201, a compound represented by Formula 202, or any combination thereof:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a),

L₂₀₅ may be *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a C₁-C₂₀ alkylene groupunsubstituted or substituted with at least one R_(10a), a C₂-C₂₀alkenylene group unsubstituted or substituted with at least one R_(10a),a C₃-C₆₀ carbocyclic group unsubstituted or substituted with at leastone R_(10a), or a C₁-C₆₀ heterocyclic group unsubstituted or substitutedwith at least one R_(10a),

xa1 to xa4 may each independently be an integer selected from 0 to 5,

xa5 may be an integer selected from 1 to 10,

R₂₀₁ to R₂₀₄, and Q₂₀₁ may each independently be a C₃-C₆₀ carbocyclicgroup unsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a),

R₂₀₁ and R₂₀₂ may optionally be linked to each other via a single bond,a C₁-C₅ alkylene group unsubstituted or substituted with at least oneR_(10a), or a C₂-C₅ alkenylene group unsubstituted or substituted withat least one R_(10a) to form a C₈-C₆₀ polycyclic group (for example, acarbazole group or the like) unsubstituted or substituted with at leastone R_(10a) (see Compound HT16 or the like),

R₂₀₃ and R₂₀₄ may optionally be linked to each other via a single bond,a C₁-C₅ alkylene group unsubstituted or substituted with at least oneR_(10a), or a C₂-C₅ alkenylene group unsubstituted or substituted withat least one R_(10a) to form a C₈-C₆₀ polycyclic group unsubstituted orsubstituted with at least one R_(10a), and

na1 may be an integer selected from 1 to 4.

In one or more embodiments, each of Formulae 201 and 202 may include atleast one of groups represented by Formulae CY201 to CY217.

In Formulae CY201 to CY217, R_(10b) and R_(10c) are each the same asdescribed in connection with R_(10a), and ring CY₂₀₁ to ring CY₂₀₄ mayeach independently be a C₃-C₂₀ carbocyclic group or a C₁-C₂₀heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217may be unsubstituted or substituted with at least one R_(10a) asdescribed in the present specification.

In an embodiment, ring CY₂₀₁ to ring CY₂₀₄ in Formulae CY201 to CY217may each independently be a benzene group, a naphthalene group, aphenanthrene group, or an anthracene group.

In one or more embodiments, each of Formulae 201 and 202 may include atleast one of groups represented by Formulae CY201 to CY203.

In one or more embodiments, Formula 201 may include at least one ofgroups represented by Formulae CY201 to CY203 and at least one of groupsrepresented by Formulae CY204 to CY217.

In one or more embodiments, in Formula 201, xa1 may be 1, R₂₀₁ may be agroup represented by one of Formulae CY201 to CY203, xa2 may be 0, andR₂₀₂ may be a group represented by one of Formulae CY204 to CY207.

In one or more embodiments, each of Formulae 201 and 202 may not includea group represented by one of Formulae CY201 to CY203.

In one or more embodiments, each of Formulae 201 and 202 may not includea group represented by one of Formulae CY201 to CY203, and may includeat least one of groups represented by Formulae CY204 to CY217.

In one or more embodiments, each of Formulae 201 and 202 may not includea group represented by one of Formulae CY201 to CY217.

In one or more embodiments, the hole transport region may include one ofCompounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD,Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD,4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combinationthereof:

A thickness of the hole transport region may be in a range of about 50 Åto about 10,000 Å, for example, about 100 Å to about 4,000 Å. When thehole transport region includes a hole injection layer, a hole transportlayer, or any combination thereof, a thickness of the hole injectionlayer may be in a range of about 100 Å to about 9,000 Å, for example,about 100 Å to about 1,000 Å, and a thickness of the hole transportlayer may be in a range of about 50 Å to about 2,000 Å, for example,about 100 Å to about 1,500 Å. When the thicknesses of the hole transportregion, the hole injection layer and the hole transport layer are withinthese ranges, suitable or satisfactory hole transporting characteristicsmay be obtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block or reduce the flow of electrons from anelectron transport region. The emission auxiliary layer and the electronblocking layer may include the materials as described above.

p-Dopant

The hole transport region may further include, in addition to the abovematerials, a charge-generation material for the improvement ofconductive properties (e.g., electrically conductive properties). Thecharge-generation material may be uniformly or non-uniformly dispersedin the hole transport region (for example, in the form of a single layerincluding (e.g., consisting of) a charge-generation material).

The charge-generation material may be, for example, a p-dopant.

In one embodiment, the lowest unoccupied molecular orbital (LUMO) energylevel of the p-dopant may be −3.5 eV or less.

In an embodiment, the p-dopant may include a quinone derivative, a cyanogroup-containing compound, a compound containing element EL1 and elementEL2, or any combination thereof.

Examples of the quinone derivative are TCNQ, F4-TCNQ, or the like.

Examples of the cyano group-containing compound are HAT-CN, and acompound represented by Formula 221 below.

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a), and

at least one of R₂₂₁ to R₂₂₃ may each independently be: a C₃-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group, each substituted witha cyano group; —F; —Cl; —Br; —I; a C₁-C₂₀ alkyl group substituted with acyano group, —F, —Cl, —Br, —I, or any combination thereof; or anycombination thereof.

In the compound containing element EL1 and element EL2, element EL1 maybe a metal, a metalloid, or a combination thereof, and element EL2 maybe a non-metal, a metalloid, or a combination thereof.

Examples of the metal are an alkali metal (for example, lithium (Li),sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); analkaline earth metal (for example, beryllium (Be), magnesium (Mg),calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal(for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V),niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten(W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium(Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni),palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au),etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin(Sn), etc.); and a lanthanide metal (for example, lanthanum (La), cerium(Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm),europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium(Ho), erbium (Er), thulium (Tm), ytterbium (Yb), ruthenium (Lu), etc.).

Examples of the metalloid are silicon (Si), antimony (Sb), and tellurium(Te).

Examples of the non-metal are oxygen (O) and halogen (for example, F,Cl, Br, I, etc.).

In an embodiment, examples of the compound containing element EL1 andelement EL2 are metal oxide, metal halide (for example, metal fluoride,metal chloride, metal bromide, and/or metal iodide), metalloid halide(for example, metalloid fluoride, metalloid chloride, metalloid bromide,and/or metalloid iodide), metal telluride, or any combination thereof.

Examples of the metal oxide are tungsten oxide (for example, WO, W₂O₃,WO₂, WO₃, W₂O₅, etc.), vanadium oxide (for example, VO, V₂O₃, VO₂, V₂O₅,etc.), molybdenum oxide (MoO, Mo₂O₃, MoO₂, MoO₃, Mo₂O₅, etc.), andrhenium oxide (for example, ReO₃, etc.).

Examples of the metal halide are alkali metal halide, alkaline earthmetal halide, transition metal halide, post-transition metal halide, andlanthanide metal halide.

Examples of the alkali metal halide are LiF, NaF, KF, RbF, CsF, LiCl,NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI,and CsI.

Examples of the alkaline earth metal halide are BeF₂, MgF₂, CaF₂, SrF₂,BaF₂, BeCl₂, MgCl₂, CaCl₂), SrCl₂, BaCl₂, BeBr₂, MgBr₂, CaBr₂, SrBr₂,BaBr₂, BeI₂, MgI₂, CaI₂, SrI₂, and BaI₂.

Examples of the transition metal halide are titanium halide (forexample, TiF₄, TiCl₄, TiBr₄, TiI₄, etc.), zirconium halide (for example,ZrF₄, ZrCl₄, ZrBr₄, ZrI₄, etc.), hafnium halide (for example, HfF₄,HfCl₄, HfBr₄, HfI₄, etc.), vanadium halide (for example, VF₃, VCl₃,VBr₃, VI₃, etc.), niobium halide (for example, NbF₃, NbCl₃, NbBr₃, NbI₃,etc.), tantalum halide (for example, TaF₃, TaCl₃, TaBr₃, TaI₃, etc.),chromium halide (for example, CrF₃, CrO₃, CrBr₃, CrI₃, etc.), molybdenumhalide (for example, MoF₃, MoCl₃, MoBr₃, MoI₃, etc.), tungsten halide(for example, WF₃, WCl₃, WBr₃, WI₃, etc.), manganese halide (forexample, MnF₂, MnCl₂, MnBr₂, MnI₂, etc.), technetium halide (forexample, TcF₂, TcCl₂, TcBr₂, TcI₂, etc.), rhenium halide (for example,ReF₂, ReCl₂, ReBr₂, ReI₂, etc.), iron halide (for example, FeF₂, FeCl₂,FeBr₂, FeI₂, etc.), ruthenium halide (for example, RuF₂, RuCl₂, RuBr₂,RuI₂, etc.), osmium halide (for example, OsF₂, OsCl₂, OsBr₂, OsI₂,etc.), cobalt halide (for example, CoF₂, COCl₂, CoBr₂, CoI₂, etc.),rhodium halide (for example, RhF₂, RhCl₂, RhBr₂, RhI₂, etc.), iridiumhalide (for example, IrF₂, IrCl₂, IrBr₂, IrI₂, etc.), nickel halide (forexample, NiF₂, NiCl₂, NiBr₂, NiI₂, etc.), palladium halide (for example,PdF₂, PdCl₂, PdBr₂, PdI₂, etc.), platinum halide (for example, PtF₂,PtCl₂, PtBr₂, PtI₂, etc.), copper halide (for example, CuF, CuCl, CuBr,CuI, etc.), silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), andgold halide (for example, AuF, AuCl, AuBr, AuI, etc.).

Examples of the post-transition metal halide are zinc halide (forexample, ZnF₂, ZnCl₂, ZnBr₂, ZnI₂, etc.), indium halide (for example,InI₃, etc.), and tin halide (for example, SnI₂, etc.).

Examples of the lanthanide metal halide are YbF, YbF₂, YbF₃, SmF₃, YbCl,YbCl₂, YbCl₃ SmCl₃, YbBr, YbBr₂, YbBr₃ SmBr₃, YbI, YbI₂, YbI₃, and SmI₃.

An example of the metalloid halide is antimony halide (for example,SbCl₅, etc.).

Examples of the metal telluride are alkali metal telluride (for example,Li₂Te, Na₂Te, K₂Te, Rb₂Te, Cs₂Te, etc.), alkaline earth metal telluride(for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metaltelluride (for example, TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃,Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe,IrTe, NiTe, PdTe, PtTe, Cu₂Te, CuTe, Ag₂Te, AgTe, Au₂Te, etc.),post-transition metal telluride (for example, ZnTe, etc.), andlanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe,EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).

Emission Layer in Interlayer 130

When the light-emitting device 10 is a full-color light-emitting device,the emission layer may be patterned into a red emission layer, a greenemission layer, and/or a blue emission layer, according to a sub-pixel.In one or more embodiments, the emission layer may have a stackedstructure of two or more layers of a red emission layer, a greenemission layer, and a blue emission layer, in which the two or morelayers contact (e.g., physically contact) each other or are separatedfrom each other. In one or more embodiments, the emission layer mayinclude two or more materials of a red light-emitting material, a greenlight-emitting material, and a blue light-emitting material, in whichthe two or more materials are mixed with each other in a single layer toemit white light.

The emission layer may include a host and a dopant. The dopant mayinclude a phosphorescent dopant, a fluorescent dopant, or anycombination thereof.

The host may include a heterocyclic compound represented by Formula 1.

The amount of the dopant in the emission layer may be from about 0.01parts by weight to about 15 parts by weight based on 100 parts by weightof the host.

In one or more embodiments, the emission layer may include a quantumdot.

In one or more embodiments, the emission layer may include a delayedfluorescence material. The delayed fluorescence material may act as ahost or a dopant in the emission layer.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within these ranges, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Host

In one or more embodiments, the host may further include a compoundrepresented by Formula 301 below.

[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21)  Formula 301

In Formula 301,

Ar301 and L₃₀₁ may each independently be a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a),

xb11 is 1, 2, or 3,

xb1 is an integer selected from 0 to 5,

R₃₀ is hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a C₁-C₆₀ alkyl group unsubstituted or substitutedwith at least one R_(10a), a C₂-C₆₀ alkenyl group unsubstituted orsubstituted with at least one R_(10a), a C₂-C₆₀ alkynyl groupunsubstituted or substituted with at least one R_(10a), a C₁-C₆₀ alkoxygroup unsubstituted or substituted with at least one R_(10a), a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least oneR_(10a), a C₁-C₆₀ heterocyclic group unsubstituted or substituted withat least one R_(10a), —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), or —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 is an integer selected from 1 to 5, and

Q₃₀₁ to Q₃₀₃ are the same as described in connection with Q₁.

In one or more embodiments, when xb11 in Formula 301 is 2 or more, twoor more of Ar₃₀₁(s) may be linked to each other via a single bond.

In an embodiment, the host may include a compound represented by Formula301-1, a compound represented by Formula 301-2, or any combinationthereof:

In Formulae 301-1 and 301-2,

ring A₃₀₁ to ring A₃₀₄ may each independently be a C₃-C₆₀ carbocyclicgroup unsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a),

X₃₀₁ may be O, S, N—[(L₃₀₄)_(xb4)-R₃₀₄], C(R₃₀₄)(R₃₀₅), orSi(R₃₀₄)(R₃₀₅),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, and R₃₀₁ are the same as described in the presentspecification,

L₃₀₂ to L₃₀₄ may each independently be the same as described inconnection with L₃₀₁,

xb2 to xb4 may each independently be the same as described in connectionwith xb1, and

R₃₀₂ to R₃₀₅ and R₃₁₁ to R₃₁₄ are the same as described in connectionwith R₃₀₁.

In one embodiment, the host may include an alkaline earth-metal complex.In an embodiment, the host may include a Be complex (for example,Compound H55), an Mg complex, a Zn complex, or a combination thereof.

In an embodiment, the host may include one of Compounds H1 to H124,9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combinationthereof:

Delayed Fluorescence Material

In one or more embodiments, the emission layer may include a delayedfluorescence material.

In the present specification, the delayed fluorescence material may beselected from compounds capable of emitting delayed fluorescence basedon a delayed fluorescence emission mechanism.

The delayed fluorescent material included in the emission layer may actas a host or a dopant depending on the type or kind of other materialsincluded in the emission layer.

In an embodiment, the difference between the triplet energy level (eV)of the delayed fluorescence material and the singlet energy level (eV)of the delayed fluorescence material may be greater than or equal to 0eV and less than or equal to 0.5 eV. When the difference between thetriplet energy level (eV) of the delayed fluorescent material and thesinglet energy level (eV) of the delayed fluorescent material satisfiesthe above-described range, up-conversion from the triplet state to thesinglet state of the delayed fluorescent materials may effectivelyoccur, and thus, the emission efficiency of the light-emitting device 10may be improved.

In an embodiment, the delayed fluorescence material may include i) amaterial including at least one electron donor (for example, a πelectron-rich C₃-C₆₀ cyclic group, such as a carbazole group) and atleast one electron acceptor (for example, a sulfoxide group, a cyanogroup, or a π electron-deficient nitrogen-containing C₁-C₆₀ cyclicgroup, etc.), and ii) a material including a C₈-C₆₀ polycyclic group inwhich two or more cyclic groups are condensed (e.g., combined togetherwith each other) while sharing boron (B).

In an embodiment, the delayed fluorescence material may include at leastone of the following compounds DF1 to DF9:

Quantum Dot

The emission layer may include a quantum dot.

In the present specification, a quantum dot refers to a crystal of asemiconductor compound, and may include any suitable material capable ofemitting light of various suitable emission wavelengths according to thesize of the crystal.

In an embodiment, a diameter of the quantum dot may be in a range ofabout 1 nm to about 10 nm.

The quantum dot may be synthesized by a wet chemical process, a metalorganic chemical vapor deposition process, a molecular beam epitaxyprocess, and/or any suitable process similar thereto.

According to the wet chemical process, a precursor material is mixedwith an organic solvent to grow a quantum dot particle crystal. When thecrystal grows, the organic solvent naturally acts as a dispersantcoordinated on the surface of the quantum dot crystal and controls thegrowth of the crystal so that the growth of quantum dot particles can becontrolled through a process which is more easily performed than vapordeposition methods, such as metal organic chemical vapor deposition(MOCVD) or molecular beam epitaxy (MBE), and which requires or has lowcosts.

The quantum dot may include: a Group III-VI semiconductor compound; aGroup II-VI semiconductor compound; a Group III-V semiconductorcompound; a Group I-III-VI semiconductor compound; a Group IV-VIsemiconductor compound; a Group IV element or compound; or anycombination thereof.

Examples of the Group II-VI semiconductor compound may include: a binarycompound, such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe,MgSe, and/or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe,ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe,CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, and/or MgZnS; aquaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS,CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and/or HgZnSTe; or any combinationthereof.

Examples of the Group III-V semiconductor compound may include: a binarycompound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP,InAs, InSb, and/or the like; a ternary compound, such as GaNP, GaNAs,GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP,InAlP, InNAs, InNSb, InPAs, InPSb, GaAlNP, and/or the like; a quaternarycompound, such as GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs,GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb,and/or the like; or any combination thereof. In one or more embodiments,the Group III-V semiconductor compound may further include Group IIelements. Examples of the Group III-V further including Group IIelements may include InZnP, InGaZnP, InAlZnP, etc.

Examples of the Group III-VI semiconductor compound may include: abinary compound, such as GaS, GaSe, Ga₂Se₃, GaTe, InS, InSe, In₂Se₃,and/or InTe; a ternary compound, such as InGaS₃, and/or InGaSe₃; or anycombination thereof.

Examples of the Group I-III-VI semiconductor compound may include: aternary compound, such as AgInS, AgInS₂, CuInS, CuInS₂, CuGaO₂, AgGaO₂,and/or AgAlO₂; or any combination thereof.

Examples of the Group IV-VI semiconductor compound may include: a binarycompound, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, and/or the like; aternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe,SnPbS, SnPbSe, SnPbTe, and/or the like; a quaternary compound, such asSnPbSSe, SnPbSeTe, SnPbSTe, and/or the like; or any combination thereof.

The Group IV element or compound may include: a single element compound,such as Si or Ge; a binary compound, such as SiC and/or SiGe; or anycombination thereof.

Each element included in a multi-element compound such as the binarycompound, ternary compound and quaternary compound, may exist in aparticle with a uniform concentration or non-uniform concentration.

In one or more embodiments, the quantum dot may have a single structureor a dual core-shell structure. In the case of the quantum dot having asingle structure, the concentration of each element included in thecorresponding quantum dot is uniform (e.g., substantially uniform). Inan embodiment, the material contained in the core and the materialcontained in the shell may be different from each other.

The shell of the quantum dot may act as a protective layer to prevent orreduce chemical degeneration of the core to maintain semiconductorcharacteristics and/or as a charging layer to impart electrophoreticcharacteristics to the quantum dot. The shell may be a single layer or amultilayer. The interface between the core and the shell may have aconcentration gradient that decreases along a direction toward thecenter of the element present in the shell.

Examples of the shell of the quantum dot may include an oxide of metal,and/or non-metal, a semiconductor compound, or any combination thereof.Examples of the oxide of metal and/or non-metal may include a binarycompound, such as SiO₂, Al₂O₃, TiO₂, ZnO, MnO, Mn₂O₃, Mn₃O₄, CuO, FeO,Fe₂O₃, Fe₃O₄, CoO, CO₃O₄, and/or NiO; a ternary compound, such asMgAl₂O₄, CoFe₂O₄, NiFe₂O₄, and/or CoMn₂O₄; or any combination thereof.Examples of the semiconductor compound may include, as described herein,a Group III-VI semiconductor compound, a Group II-VI semiconductorcompounds, a Group III-V semiconductor compounds, a Group I-III-VIsemiconductor compounds; a Group IV-VI semiconductor compounds; and anycombination thereof. In addition, the semiconductor compound may includeCdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS,HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combinationthereof.

A full width at half maximum (FWHM) of an emission wavelength spectrumof the quantum dot may be about 45 nm or less, for example, about 40 nmor less, for example, about 30 nm or less. In addition, because thelight emitted through the quantum dot is emitted in all directions, thewide viewing angle can be improved.

In addition, the quantum dot may be, for example, a sphericalnanoparticle, a pyramidal nanoparticle, a multi-arm nanoparticle, acubic nanoparticle, a nanotube particle, a nanowire particle, ananofiber particle, and/or a nanoplate particle.

Because the energy band gap can be adjusted by controlling the size ofthe quantum dot, light having various suitable wavelength bands can beobtained from the quantum dot emission layer. Therefore, by usingquantum dots of different sizes, a light-emitting display that emitslight of various suitable wavelengths may be implemented. In oneembodiment, the size of the quantum dot may be selected from to emitred, green and/or blue light. In addition, the size of the quantum dotmay emit white light by combining light of various suitable colors.

Electron Transport Region in Interlayer 130

The electron transport region may have: i) a single-layered structureincluding (e.g., consisting of) a single layer including (e.g.,consisting of) a single material, ii) a single-layered structureincluding (e.g., consisting of) a single layer including (e.g.,consisting of) a plurality of different materials, or iii) amulti-layered structure including a plurality of layers includingdifferent materials.

The electron transport region may include a buffer layer, a holeblocking layer, an electron control layer, an electron transport layer,an electron injection layer, or any combination thereof.

In an embodiment, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein, for each structure, constituting layers aresequentially stacked from an emission layer.

In an embodiment, the electron transport region (for example, the bufferlayer, the hole blocking layer, the electron control layer, or theelectron transport layer in the electron transport region) may include ametal-free compound including at least one π electron-deficientnitrogen-containing C₁-C₆₀ cyclic group.

In an embodiment, the electron transport region may include a compoundrepresented by Formula 601 below:

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21).  Formula 601

In Formula 601,

Ar₆₀₁ and L₆₀₁ may each independently be a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a),

xe11 may be 1, 2, or 3,

xe1 may be 0, 1, 2, 3, 4, or 5,

R₆₀₁ may be a C₃-C₆₀ carbocyclic group unsubstituted or substituted withat least one R_(10a), a C₁-C₆₀ heterocyclic group unsubstituted orsubstituted with at least one R_(10a), —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃),—C(═O)(Q₆₀₁), —S(═O)₂(Q₆₀₁), or —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ are the same as described in connection with Q₁,

xe21 may be 1, 2, 3, 4, or 5, and

at least one of Ar₆₀₁, L₆₀₁, and R₆₀₁ may each independently be a πelectron-deficient nitrogen-containing C₁-C₆₀ cyclic group unsubstitutedor substituted with at least one R_(10a).

In an embodiment, when xe11 in Formula 601 is 2 or more, two or more ofAr₆₀₁(s) may be linked via a single bond.

In an embodiment, Ar₆₀₁ in Formula 601 may be a substituted orunsubstituted anthracene group.

In an embodiment, the electron transport region may include a compoundrepresented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), at least one of X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ are the same as described in connection with L₆₀₁,

xe611 to xe613 are the same as described in connection with xe1,

R₆₁₁ to R₆₁₃ are the same as described in connection with R₆₀₁,

R₆₁₄ to R₆₁₆ may each independently be hydrogen, deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a C₃-C₆₀ carbocyclic group unsubstitutedor substituted with at least one R_(10a), or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a).

In an embodiment, xe1 and xe611 to xe613 in Formulae 601 and 601-1 mayeach independently be 0, 1, or 2.

The electron transport region may include one of Compounds ET1 to ET45,2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq, TAZ, NTAZ, or anycombination thereof:

The thickness of the electron transport region may be from about 160 Åto about 5,000 Å, for example, from about 100 Å to about 4,000 Å. Whenthe electron transport region includes a buffer layer, a hole blockinglayer, an electron control layer, an electron transport layer, or anycombination thereof, the thickness of the buffer layer, the holeblocking layer, or the electron control layer may each independently befrom about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å,and the thickness of the electron transport layer may be from about 100Å to about 1000 Å, for example, about 150 Å to about 500 Å. When thethicknesses of the buffer layer, hole blocking layer, electron controllayer, electron transport layer and/or electron transport layer arewithin these ranges, suitable or satisfactory hole transportingcharacteristics may be obtained without a substantial increase indriving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include an alkali metal complex,alkaline earth metal complex, or any combination thereof. A metal ion ofthe alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion,or a Cs ion, and a metal ion of the alkaline earth metal complex may bea Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligandcoordinated with the metal ion of the alkali metal complex or thealkaline earth-metal complex may each independently include ahydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, ahydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, ahydroxyphenylthiazole, a hydroxydiphenyloxadiazole, ahydroxydiphenylthiadiazole, a hydroxyphenylpyridine, ahydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine,a phenanthroline, a cyclopentadiene, or any combination thereof.

In an embodiment, the metal-containing material may include a Licomplex. The Li complex may include, for example, Compound ET-D1 (LiQ)or ET-D2:

The electron transport region may include an electron injection layerthat facilitates the injection of electrons from the second electrode150. The electron injection layer may directly contact (e.g., physicallycontact) the second electrode 150.

The electron injection layer may have: i) a single-layered structureincluding (e.g., consisting of) a single layer including (e.g.,consisting of) a single material, ii) a single-layered structureincluding (e.g., consisting of) a single layer including (e.g.,consisting of) a plurality of different materials, or iii) amulti-layered structure including a plurality of layers includingdifferent materials.

The electron injection layer may include an alkali metal, alkaline earthmetal, a rare earth metal, an alkali metal-containing compound, alkalineearth metal-containing compound, a rare earth metal-containing compound,an alkali metal complex, alkaline earth metal complex, a rare earthmetal complex, or any combination thereof.

The alkali metal may include Li, Na, K, Rb, Cs, or any combinationthereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or anycombination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb,Gd, or any combination thereof.

The alkali metal-containing compound, the alkaline earthmetal-containing compound, and the rare earth metal-containing compoundmay be oxides, halides (for example, fluorides, chlorides, bromides,and/or iodides), and/or tellurides of the alkali metal, the alkalineearth metal, and/or the rare earth metal, or any combination thereof.

The alkali metal-containing compound may include alkali metal oxides,such as Li₂O, Cs₂O, and/or K₂O, alkali metal halides, such as LiF, NaF,CsF, KF, LiI, NaI, CsI, and/or KI, or any combination thereof. Thealkaline earth metal-containing compound may include an alkaline earthmetal compound, such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (x is a realnumber satisfying the condition of 0<x<1), Ba_(x)Ca_(1-x)O (x is a realnumber satisfying the condition of 0<x<1), and/or the like. The rareearth metal-containing compound may include YbF₃, ScF₃, Sc₂O₃, Y₂O₃,Ce₂O₃, GdF₃, TbF₃, YbI₃, ScI₃, TbI₃, or any combination thereof. In anembodiment, the rare earth metal-containing compound may includelanthanide metal telluride. Examples of the lanthanide metal tellurideare LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe,ErTe, TmTe, YbTe, LuTe, La₂Te₃, Ce₂Te₃, Pr₂Te₃, Nd₂Te₃, Pm₂Te₃, Sm₂Te₃,Eu₂Te₃, Gd₂Te₃, Tb₂Te₃, Dy₂Te₃, Ho₂Te₃, Er₂Te₃, Tm₂Te₃, Yb₂Te₃, andLu₂Te₃.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include i) one of ions of the alkali metal, thealkaline earth metal, and the rare earth metal and ii), as a ligandbonded to the metal ion, for example, hydroxyquinoline,hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine,hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole,hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole,hydroxyphenylpyridine, hydroxyphenyl benzimidazole,hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene,or any combination thereof.

The electron injection layer may include (e.g., consist of) an alkalimetal, an alkaline earth metal, a rare earth metal, an alkalimetal-containing compound, an alkaline earth metal-containing compound,a rare earth metal-containing compound, an alkali metal complex, analkaline earth metal complex, a rare earth metal complex, or anycombination thereof, as described above. In an embodiment, the electroninjection layer may further include an organic material (for example, acompound represented by Formula 601).

In an embodiment, the electron injection layer may include (e.g.,consist of) i) an alkali metal-containing compound (for example, analkali metal halide), ii) a) an alkali metal-containing compound (forexample, an alkali metal halide); and b) an alkali metal, an alkalineearth metal, a rare earth metal, or any combination thereof. In anembodiment, the electron injection layer may be a KI:Yb co-depositedlayer, an RbI:Yb co-deposited layer, and/or the like.

When the electron injection layer further includes an organic material,alkali metal, alkaline earth metal, rare earth metal, an alkalimetal-containing compound, an alkaline earth metal-containing compound,a rare earth metal-containing compound, alkali metal complex, alkalineearth-metal complex, rare earth metal complex, or any combinationthereof may be homogeneously or non-homogeneously dispersed in a matrixincluding the organic material.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the range describedabove, the electron injection layer may have suitable or satisfactoryelectron injection characteristics without a substantial increase indriving voltage.

Second Electrode 150

The second electrode 150 may be located on the interlayer 130 havingsuch a structure. The second electrode 150 may be a cathode, which is anelectron injection electrode, and as the material for the secondelectrode 150, a metal, an alloy, an electrically conductive compound,or any combination thereof, each having a low work function, may beused.

In an embodiment, the second electrode 150 may include at least oneselected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO,IZO, or a combination thereof. The second electrode 150 may be atransmissive electrode, a semi-transmissive electrode, or a reflectiveelectrode.

The second electrode 150 may have a single-layered structure or amulti-layered structure including two or more layers.

Capping Layer

A first capping layer may be located outside the first electrode 110,and/or a second capping layer may be outside the second electrode 150.In more detail, the light-emitting device 10 may have a structure inwhich the first capping layer, the first electrode 110, the interlayer130, and the second electrode 150 are sequentially stacked in thisstated order, a structure in which the first electrode 110, theinterlayer 130, the second electrode 150, and the second capping layerare sequentially stacked in this stated order, or a structure in whichthe first capping layer, the first electrode 110, the interlayer 130,the second electrode 150, and the second capping layer are sequentiallystacked in this stated order.

Light generated in an emission layer of the interlayer 130 of thelight-emitting device 10 may be extracted toward the outside through thefirst electrode 110, which is a semi-transmissive electrode or atransmissive electrode, and the first capping layer or light generatedin an emission layer of the interlayer 130 of the light-emitting device10 may be extracted toward the outside through the second electrode 150,which is a semi-transmissive electrode or a transmissive electrode, andthe second capping layer.

The first capping layer and the second capping layer may increaseexternal emission efficiency according to the principle of constructiveinterference. Accordingly, the light extraction efficiency of thelight-emitting device 10 is increased, so that the emission efficiencyof the light-emitting device 10 may be improved.

Each of the first capping layer and second capping layer may include amaterial having a refractive index (at a wavelength of 589 nm) of 1.6 ormore.

The first capping layer and the second capping layer may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial.

At least one selected from the first capping layer and the secondcapping layer may each independently include carbocyclic compounds,heterocyclic compounds, an amine group-containing compounds, porphyrinederivatives, phthalocyanine derivatives, a naphthalocyanine derivatives,alkali metal complexes, alkaline earth-based complexes, or anycombination thereof. The carbocyclic compound, the heterocycliccompound, and the amine group-containing compound may be optionallysubstituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I,or any combination thereof. In an embodiment, at least one of the firstcapping layer and the second capping layer may each independentlyinclude an amine group-containing compound.

In an embodiment, at least one of the first capping layer and the secondcapping layer may each independently include a compound represented byFormula 201, a compound represented by Formula 202, or any combinationthereof.

In one or more embodiments, at least one of the first capping layer andthe second capping layer may each independently include a compoundselected from Compounds HT28 to HT33, Compounds CP1 to CP6, β-NPB, orany combination thereof, but embodiments of the present disclosure arenot limited thereto:

Electronic Apparatus

The light-emitting device may be included in various suitable electronicapparatuses. In an embodiment, the electronic apparatus including thelight-emitting device may be a light-emitting apparatus, anauthentication apparatus, and/or the like.

The electronic apparatus (for example, light-emitting apparatus) mayfurther include, in addition to the light-emitting device, i) a colorfilter, ii) a color conversion layer, or iii) a color filter and a colorconversion layer. The color filter and/or the color conversion layer maybe located in at least one traveling direction of light emitted from thelight-emitting device. In an embodiment, the light emitted from thelight-emitting device may be blue light or white light. Thelight-emitting device may be the same as described above. In anembodiment, the color conversion layer may include quantum dots. In anembodiment, the quantum dot may be a quantum dot as described herein.

The electronic apparatus may include a first substrate. The firstsubstrate may include a plurality of subpixel areas, the color filtermay include a plurality of color filter areas respectively correspondingto the subpixel areas, and the color conversion layer may include aplurality of color conversion areas respectively corresponding to thesubpixel areas.

A pixel-defining film may be located among the subpixel areas to defineeach of the subpixel areas.

The color filter may further include a plurality of color filter areasand a light-blocking patterns located among the color filter areas, andthe color conversion layer may include a plurality of color conversionareas and light-blocking patterns located among the color conversionareas.

The color filter areas (or the color conversion areas) may include afirst area that emits a first color light, a second area that emits asecond color light, and/or a third area that emits a third color light,and the first color light, the second color light, and/or the thirdcolor light may have different maximum emission wavelengths from oneanother. In an embodiment, the first color light may be red light, thesecond color light may be green light, and the third color light may beblue light. In an embodiment, the color filter areas (or the colorconversion areas) may include quantum dots. In more detail, the firstarea may include a red quantum dot, the second area may include a greenquantum dot, and the third area may not include a quantum dot. Thequantum dot is the same as described in the present specification. Thefirst area, the second area, and/or the third area may each include ascatterer (e.g., a light scatterer).

In an embodiment, the light-emitting device may emit a first light, thefirst area may absorb the first light and emit a first first-colorlight, the second area may absorb the first light and emit a secondfirst-color light, and the third area may absorb the first light andemit a third first-color light. In this regard, the first first-colorlight, the second first-color light, and the third first-color light mayhave different maximum emission wavelengths from one another. In moredetail, the first light may be blue light, the first first-color lightmay be red light, the second first-color light may be green light, andthe third first-color light may be blue light.

The electronic apparatus may further include a thin-film transistor inaddition to the light-emitting device 10 as described above. Thethin-film transistor may include a source electrode, a drain electrode,and an activation layer, wherein any one selected from the sourceelectrode and the drain electrode may be electrically coupled to any oneselected from the first electrode and the second electrode of thelight-emitting device.

The thin-film transistor may include a gate electrode, a gate insulatingfilm, etc.

The activation layer may include crystalline silicon, amorphous silicon,organic semiconductor, oxide semiconductor, and/or the like.

The electronic apparatus may further include a sealing portion forsealing the light-emitting device. The sealing portion and/or the colorconversion layer may be placed between the color filter and thelight-emitting device. The sealing portion allows light from thelight-emitting device to be extracted to the outside, while concurrently(e.g., simultaneously) preventing or reducing penetration of ambient airand/or moisture into the light-emitting device. The sealing portion maybe a sealing substrate including a transparent glass and/or a plasticsubstrate. The sealing portion may be a thin-film encapsulation layerincluding at least one layer of an organic layer and/or an inorganiclayer. When the sealing portion is a thin film encapsulation layer, theelectronic apparatus may be flexible.

Various suitable functional layers may be additionally located on thesealing portion, in addition to the color filter and/or the colorconversion layer, according to the use of the electronic apparatus. Thefunctional layers may include a touch screen layer, a polarizing layer,and/or the like. The touch screen layer may be a pressure-sensitivetouch screen layer, a capacitive touch screen layer, and/or an infra-redtouch screen layer. In an embodiment, the authentication apparatus maybe a biometric authentication apparatus that authenticates an individualby using biometric information of a living body (for example,fingertips, pupils, etc.).

The authentication apparatus may further include, in addition to thelight-emitting device, a biometric information collector.

The electronic apparatus may be applied to various suitable displays,light sources, lighting, personal computers (for example, a mobilepersonal computer), mobile phones, digital cameras, electronicorganizers, electronic dictionaries, electronic game machines, medicalinstruments (for example, electronic thermometers, sphygmomanometers,blood glucose meters, pulse measurement devices, pulse wave measurementdevices, electrocardiogram displays, ultrasonic diagnostic devices,and/or endoscope displays), fish finders, various suitable measuringinstruments, meters (for example, meters for a vehicle, an aircraft,and/or a vessel), projectors, and/or the like.

Description of FIGS. 2 and 3

FIG. 2 is a cross-sectional view showing a light-emitting apparatusaccording to an embodiment of the present disclosure.

The light-emitting apparatus of FIG. 2 includes a substrate 100, athin-film transistor (TFT), a light-emitting device, and anencapsulation portion 300 that seals the light-emitting device.

The substrate 100 may be a flexible substrate, a glass substrate, and/ora metal substrate. A buffer layer 210 may be formed on the substrate100. The buffer layer 210 may prevent or reduce penetration ofimpurities through the substrate 100 and may provide a flat surface onthe substrate 100.

A TFT may be located on the buffer layer 210. The TFT may include anactivation layer 220, a gate electrode 240, a source electrode 260, anda drain electrode 270.

The activation layer 220 may include an inorganic semiconductor such assilicon and/or polysilicon, an organic semiconductor, and/or an oxidesemiconductor, and may include a source region, a drain region and achannel region.

A gate insulating film 230 for insulating the activation layer 220 fromthe gate electrode 240 may be located on the activation layer 220, andthe gate electrode 240 may be located on the gate insulating film 230.

An interlayer insulating film 250 is located on the gate electrode 240.The interlayer insulating film 250 may be placed between the gateelectrode 240 and the source electrode 260 to insulate the gateelectrode 240 from the source electrode 260 and between the gateelectrode 240 and the drain electrode 270 to insulate the gate electrode240 from the drain electrode 270.

The source electrode 260 and the drain electrode 270 may be located onthe interlayer insulating film 250. The interlayer insulating film 250and the gate insulating film 230 may be formed to expose the sourceregion and the drain region of the activation layer 220, and the sourceelectrode 260 and the drain electrode 270 may be in contact (e.g.,physical contact) with the exposed portions of the source region and thedrain region of the activation layer 220.

The TFT is electrically coupled to a light-emitting device to drive thelight-emitting device, and is covered by a passivation layer 280. Thepassivation layer 280 may include an inorganic insulating film, anorganic insulating film, or a combination thereof. A light-emittingdevice is provided on the passivation layer 280. The light-emittingdevice may include a first electrode 110, an interlayer 130, and asecond electrode 150.

The first electrode 110 may be on the passivation layer 280. Thepassivation layer 280 does not completely cover the drain electrode 270and exposes a portion of the drain electrode 270, and the firstelectrode 110 is coupled to the exposed portion of the drain electrode270.

A pixel defining layer 290 containing an insulating material may be onthe first electrode 110. The pixel defining layer 290 exposes a regionof the first electrode 110, and an interlayer 130 may be in the exposedregion of the first electrode 110. The pixel defining layer 290 may be apolyimide and/or polyacrylic organic film. In one or more embodiments,at least some layers of the interlayer 130 may extend beyond the upperportion of the pixel defining layer 290 to be in the form of a commonlayer.

The second electrode 150 may be on the interlayer 130, and a cappinglayer 170 may be additionally on the second electrode 150. The cappinglayer 170 may cover the second electrode 150.

The encapsulation portion 300 may be on the capping layer 170. Theencapsulation portion 300 may be on a light-emitting device to protectthe light-emitting device from moisture and/or oxygen. The encapsulationportion 300 may include: an inorganic film including silicon nitride(SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, orany combination thereof; an organic film including polyethyleneterephthalate, polyethylene naphthalate, polycarbonate, polyimide,polyethylene sulfonate, polyoxymethylene, polyarylate,hexamethyldisiloxane, an acrylic resin (for example, polymethylmethacrylate, polyacrylic acid, and/or the like), an epoxy-based resin(for example, aliphatic glycidyl ether (AGE), and/or the like), or acombination thereof; or a combination of the inorganic film and theorganic film.

FIG. 3 shows a cross-sectional view showing a light-emitting apparatusaccording to an embodiment of the present disclosure.

The light-emitting apparatus of FIG. 3 is substantially the same as thelight-emitting apparatus of FIG. 2, except that a light-blocking pattern500 and a functional region 400 are additionally on the encapsulationportion 300. The functional region 400 may be a combination of i) acolor filter area, ii) a color conversion area, or iii) a combination ofthe color filter area and the color conversion area. In an embodiment,the light-emitting device included in the light-emitting apparatus ofFIG. 3 may be a tandem light-emitting device.

Manufacture Method

Respective layers included in the hole transport region, the emissionlayer, and respective layers included in the electron transport regionmay be formed in a certain region by using one or more suitable methodsselected from vacuum deposition, spin coating, casting,Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, andlaser-induced thermal imaging.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed byvacuum deposition, the deposition may be performed at a depositiontemperature of about 100° C. to about 500° C., a vacuum degree of about10⁻⁸ torr to about 10⁻³ torr, and a deposition speed of about 0.01 Å/secto about 100 Å/sec, depending on a material to be included in a layer tobe formed and the structure of a layer to be formed.

Definition of Terms

The term “C₃-C₆₀ carbocyclic group,” as used herein, refers to a cyclicgroup consisting of carbon atoms only and having three to sixty carbonatoms, and the term “C₁-C₆₀ heterocyclic group,” as used herein, refersto a cyclic group that has one to sixty carbon atoms and further has, inaddition to carbon, a heteroatom. The C₃-C₆₀ carbocyclic group and theC₁-C₆₀ heterocyclic group may each be a monocyclic group consisting ofone ring or a polycyclic group in which two or more rings are condensedwith each other (e.g., combined together with each other). In anembodiment, the number of ring-forming atoms of the C₁-C₆₀ heterocyclicgroup may be from 3 to 61.

The “cyclic group,” as used herein, may include the C₃-C₆₀ carbocyclicgroup, and the C₁-C₆₀ heterocyclic group.

The term “π electron-rich C₃-C₆₀ cyclic group,” as used herein, refersto a cyclic group that has three to sixty carbon atoms and does notinclude *—N═*′ as a ring-forming moiety, and the term “πelectron-deficient nitrogen-containing C₁-C₆₀ cyclic group,” as usedherein, refers to a heterocyclic group that has one to sixty carbonatoms and includes *—N═*′ as a ring-forming moiety.

In an embodiment,

the C₃-C₆₀ carbocyclic group may be i) group T1 or ii) a condensedcyclic group in which two or more groups T1 are condensed with (e.g.,combined together with) each other (for example, a cyclopentadienegroup, an adamantane group, a norbornane group, a benzene group, apentalene group, a naphthalene group, an azulene group, an indacenegroup, acenaphthylene group, a phenalene group, a phenanthrene group, ananthracene group, a fluoranthene group, a triphenylene group, a pyrenegroup, a chrysene group, a perylene group, a pentaphene group, aheptalene group, a naphthacene group, a picene group, a hexacene group,a pentacene group, a rubicene group, a coronene group, an ovalene group,an indene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, an indenophenanthrene group, or an indenoanthracenegroup),

the C₁-C₆₀ heterocyclic group may be i) group T2, ii) a condensed cyclicgroup in which two or more groups T2 are condensed with (e.g., combinedtogether with) each other, or iii) a condensed cyclic group in which atleast one group T2 and at least one group T1 are condensed with (e.g.,combined together with) each other (for example, a pyrrole group, athiophene group, a furan group, an indole group, a benzoindole group, anaphthon indole group, an isoindole group, a benzoisoindole group, anaphthon isoindole group, a benzosilole group, a benzothiophene group, abenzofuran group, a carbazole group, a dibenzosilole group, adibenzothiophene group, a dibenzofuran group, an indenocarbazole group,an indolocarbazole group, a benzofurocarbazole group, abenzothienocarbazole group, a benzosilolocarbazole group, abenzoindolocarbazole group, a benzocarbazole group, a benzonaphthofurangroup, a benzonaphthothiophene group, a benzonaphthosilole group, abenzofurodibenzofuran group, a benzofurodibenzothiophene group, abenzothienodibenzothiophene group, a pyrazole group, an imidazole group,a triazole group, an oxazole group, an isoxazole group, an oxadiazolegroup, a thiazole group, an isothiazole group, a thiadiazole group, abenzopyrazole group, a benzimidazole group, a benzoxazole group, abenzoisoxazole group, a benzothiazole group, a benzoisothiazole group, apyridine group, a pyrimidine group, a pyrazine group, a pyridazinegroup, a triazine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a benzoisoquinoline group, a quinoxaline group, abenzoquinoxaline group, a quinazoline group, a benzoquinazoline group, aphenanthroline group, a cinnoline group, a phthalazine group, anaphthyridine group, an imidazopyridine group, an imidazopyrimidinegroup, an imidazotriazine group, an imidazopyrazine group, animidazopyridazine group, an azacarbazole group, an azafluorene group, anazadibenzosilole group, an azadibenzothiophene group, an azadibenzofurangroup, etc.),

the π electron-rich C₃-C₆₀ cyclic group may be i) group T1, ii) acondensed cyclic group in which two or more groups T1 are condensed with(e.g., combined together with) each other, iii) group T3, iv) acondensed cyclic group in which two or more groups T3 are condensed with(e.g., combined together with) each other, or v) a condensed cyclicgroup in which at least one group T3 and at least one group T1 arecondensed with (e.g., combined together with) each other (for example,the C₃-C₆₀ carbocyclic group, a pyrrole group, a thiophene group, afuran group, an indole group, a benzoindole group, a naphthon indolegroup, an isoindole group, a benzoisoindole group, a naphthon isoindolegroup, a benzosilole group, a benzothiophene group, a benzofuran group,a carbazole group, a dibenzosilole group, a dibenzothiophene group, adibenzofuran group, an indenocarbazole group, an indolocarbazole group,a benzofurocarbazole group, a benzothienocarbazole group, abenzosilolocarbazole group, a benzoindolocarbazole group, abenzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophenegroup, a benzonaphthosilole group, a benzofurodibenzofuran group, abenzofurodibenzothiophene group, a benzothienodibenzothiophene group,etc.),

the π electron-deficient nitrogen-containing C₁-C₆₀ cyclic group may bei) group T4, ii) a condensed cyclic group in which two or more group T4are condensed with (e.g., combined together with) each other, iii) acondensed cyclic group in which at least one group T4 and at least onegroup T1 are condensed with (e.g., combined together with) each other,iv) a condensed cyclic group in which at least one group T4 and at leastone group T3 are condensed with (e.g., combined together with) eachother, or v) a condensed cyclic group in which at least one group T4, atleast one group T1, and at least one group T3 are condensed with (e.g.,combined together with) one another (for example, a pyrazole group, animidazole group, a triazole group, an oxazole group, an isoxazole group,an oxadiazole group, a thiazole group, an isothiazole group, athiadiazole group, a benzopyrazole group, a benzimidazole group, abenzoxazole group, a benzoisoxazole group, a benzothiazole group, abenzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazinegroup, a pyridazine group, a triazine group, a quinoline group, anisoquinoline group, a benzoquinoline group, a benzoisoquinoline group, aquinoxaline group, a benzoquinoxaline group, a quinazoline group, abenzoquinazoline group, a phenanthroline group, a cinnoline group, aphthalazine group, a naphthyridine group, an imidazopyridine group, animidazopyrimidine group, an imidazotriazine group, an imidazopyrazinegroup, an imidazopyridazine group, an azacarbazole group, an azafluorenegroup, an azadibenzosilole group, an azadibenzothiophene group, anazadibenzofuran group, etc.),

group T1 may be a cyclopropane group, a cyclobutane group, acyclopentane group, a cyclohexane group, a cycloheptane group, acyclooctane group, a cyclobutene group, a cyclopentene group, acyclopentadiene group, a cyclohexene group, a cyclohexadiene group, acycloheptene group, an adamantane group, a norbornane (or abicyclo[2.2.1]heptane) group, a norbornene group, abicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, abicyclo[2.2.2]octane group, or a benzene group,

group T2 may be a furan group, a thiophene group, a 1H-pyrrole group, asilole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, animidazole group, a pyrazole group, a triazole group, a tetrazole group,an oxazole group, an isoxazole group, an oxadiazole group, a thiazolegroup, an isothiazole group, a thiadiazole group, an azasilole group, anazaborole group, a pyridine group, a pyrimidine group, a pyrazine group,a pyridazine group, a triazine group, or a tetrazine group,

group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, asilole group, or a borole group, and

group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazolegroup, a pyrazole group, a triazole group, a tetrazole group, an oxazolegroup, an isoxazole group, an oxadiazole group, a thiazole group, anisothiazole group, a thiadiazole group, an azasilole group, an azaborolegroup, a pyridine group, a pyrimidine group, a pyrazine group, apyridazine group, a triazine group, or a tetrazine group.

The terms “the cyclic group,” “the C₃-C₆₀ carbocyclic group,” “theC₁-C₆₀ heterocyclic group,” “the π electron-rich C₃-C₆₀ cyclic group,”or “the π electron-deficient nitrogen-containing C₁-C₆₀ cyclic group,”as used herein, refer to a group condensed to (e.g., combined togetherwith) any suitable cyclic group or a polyvalent group (for example, adivalent group, a trivalent group, a tetravalent group, etc.), dependingon the structure of a formula in connection with which the terms areused. In an embodiment, “a benzene group” may be a benzo group, a phenylgroup, a phenylene group, or the like, which may be easily understand byone of ordinary skill in the art according to the structure of a formulaincluding the “benzene group.”

Examples of the monovalent C₃-C₆₀ carbocyclic group and the monovalentC₁-C₆₀ heterocyclic group may include a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group, and examplesof the divalent C₃-C₆₀ carbocyclic group and the monovalent C₁-C₆₀heterocyclic group may include a C₃-C₁₀ cycloalkylene group, a C₁-C₁₀heterocycloalkylene group, a C₃-C₁₀ cycloalkenylene group, a C₁-C₁₀heterocycloalkenylene group, a C₆-C₆₀ arylene group, a C₁-C₆₀heteroarylene group, a divalent non-aromatic condensed polycyclic group,and a substituted or unsubstituted divalent non-aromatic condensedheteropolycyclic group.

The term “C₁-C₆₀ alkyl group,” as used herein, refers to a linear orbranched aliphatic hydrocarbon monovalent group that has one to sixtycarbon atoms, and examples thereof include a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, asec-butyl group, an isobutyl group, a tert-butyl group, an n-pentylgroup, a tert-pentyl group, neopentyl group, an isopentyl group, asec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexylgroup, an isohexyl group, a sec-hexyl group, a tert-hexyl group, ann-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptylgroup, an n-octyl group, an isooctyl group, a sec-octyl group, atert-octyl group, an n-nonyl group, an isononyl group, a sec-nonylgroup, a tert-nonyl group, an n-decyl group, an isodecyl group, asec-decyl group, and a tert-decyl group. The term “C₁-C₆₀ alkylenegroup,” as used herein, refers to a divalent group having substantiallythe same structure as the C₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group,” as used herein, refers to a monovalenthydrocarbon group having at least one carbon-carbon double bond at amain chain (e.g., in the middle) or at a terminal end (e.g., theterminus) of the C₂-C₆₀ alkyl group, and examples thereof include anethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group,” as used herein, refers to a divalent group havingsubstantially the same structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group,” as used herein, refers to a monovalenthydrocarbon group having at least one carbon-carbon triple bond at amain chain (e.g., in the middle) or at a terminal end (e.g., theterminus) of the C₂-C₆₀ alkyl group, and examples thereof include anethynyl group and a propynyl group. The term “C₂-C₆₀ alkynylene group,”as used herein, refers to a divalent group having substantially the samestructure as the C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group,” as used herein, refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group,” as used herein, refers to amonovalent saturated hydrocarbon cyclic group having 3 to 10 carbonatoms, and examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group (or abicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, abicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term“C₃-C₁₀ cycloalkylene group,” as used herein, refers to a divalent grouphaving substantially the same structure as the C₃-C₁a cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group,” as used herein, refers to amonovalent cyclic group that further includes, in addition to a carbonatom, at least one heteroatom as a ring-forming atom and has 1 to 10carbon atoms, and examples thereof include a 1,2,3,4-oxatriazolidinylgroup, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. Theterm “C₁-C₁₀ heterocycloalkylene group,” as used herein, refers to adivalent group having substantially the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group,” as used herein, refers to amonovalent cyclic group that has three to ten carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity(e.g., is not aromatic), and examples thereof include a cyclopentenylgroup, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group,” as used herein, refers to a divalent grouphaving substantially the same structure as the C₃-C₁₀ cycloalkenylgroup.

The term “C₁-C₁₀ heterocycloalkenyl group,” as used herein, refers to amonovalent cyclic group that has, in addition to a carbon atom, at leastone heteroatom as a ring-forming atom, 1 to 10 carbon atoms, and atleast one carbon-carbon double bond in the cyclic structure thereof.Examples of the C₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup,” as used herein, refers to a divalent group having substantiallythe same structure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group,” as used herein, refers to a monovalentgroup having a carbocyclic aromatic system having six to sixty carbonatoms, and the term “C₆-C₆₀ arylene group,” as used herein, refers to adivalent group having a carbocyclic aromatic system having six to sixtycarbon atoms. Examples of the C₆-C₆₀ aryl group include a fluorenylgroup, a phenyl group, a pentalenyl group, a naphthyl group, an azulenylgroup, an indacenyl group, an acenaphthyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenylgroup, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, apicenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group,a coronenyl group, and an ovalenyl group. When the C₆-C₆₀ aryl group andthe C₆-C₆₀ arylene group each include two or more rings, the rings maybe condensed with each other (e.g., combined together with each other).

The term “C₁-C₆₀ heteroaryl group,” as used herein, refers to amonovalent group having a heterocyclic aromatic system that has, inaddition to a carbon atom, at least one heteroatom as a ring-formingatom, and 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group,”as used herein, refers to a divalent group having a heterocyclicaromatic system that has, in addition to a carbon atom, at least oneheteroatom as a ring-forming atom, and 1 to 60 carbon atoms. Examples ofthe C₁-C₆₀ heteroaryl group include a carbazolyl group, a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, a benzoquinolinyl group, anisoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, abenzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinylgroup, a cinnolinyl group, a phenanthrolinyl group, a phthalazinylgroup, and a naphthyridinyl group. When the C₁-C₆₀ heteroaryl group andthe C₁-C₆₀ heteroarylene group each include two or more rings, the ringsmay be condensed with each other (e.g., combined together with eachother).

The term “monovalent non-aromatic condensed polycyclic group,” as usedherein, refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed to each other (e.g., combinedtogether with each other), only carbon atoms as ring-forming atoms, andnon-aromaticity in its entire molecular structure (e.g., when consideredas a whole the entire molecular structure is not aromatic). Examples ofthe monovalent non-aromatic condensed polycyclic group include anindenyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, an indenophenanthrenyl group, and an indenonanthracenyl group. The term “divalent non-aromatic condensed polycyclicgroup,” as used herein, refers to a divalent group having substantiallythe same structure as a monovalent non-aromatic condensed polycyclicgroup.

The term “monovalent non-aromatic condensed heteropolycyclic group,” asused herein, refers to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other (e.g.,combined together with each other), at least one heteroatom other thancarbon atoms, as a ring-forming atom, and non-aromaticity in its entiremolecular structure (e.g., when considered as a whole the entiremolecular structure is not aromatic). Examples of the monovalentnon-aromatic condensed heteropolycyclic group include a pyrrolyl group,a thiophenyl group, a furanyl group, an indolyl group, a benzoindolylgroup, a naphthon indolyl group, an isoindolyl group, a benzoisoindolylgroup, a naphthoisoindolyl group, a benzosilolyl group, abenzothiophenyl group, a benzofuranyl group, a carbazolyl group, adibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group,an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolylgroup, an azadibenzothiophenyl group, an azadibenzofuranyl group, apyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolylgroup, an oxazolyl group, an isoxazolyl group, a thiazolyl group, anisothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, abenzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, abenzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolylgroup, an imidazopyridinyl group, an imidazopyrimidinyl group, animidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinylgroup, an indeno carbazolyl group, an indolocarbazolyl group, abenzofurocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, a benzoindolocarbazolyl group, abenzocarbazolyl group, a benzonaphthofuranyl group, abenzonaphthothiophenyl group, a benzonaphtho silolyl group, abenzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and abenzothienodibenzothiophenyl group. The term “divalent non-aromaticheterocondensed polycyclic group,” as used herein, refers to a divalentgroup having substantially the same structure as a monovalentnon-aromatic heterocondensed polycyclic group.

The term “C₆-C₆₀ aryloxy group,” as used herein, indicates —OA₁₀₂(wherein A₁₀₂ is the C₆-C₆₀ aryl group), and the term “C₆-C₆₀ arylthiogroup,” as used herein, indicates —SA₁₀₃(wherein A₁₀₃ is the C₆-C₆₀ arylgroup).

The term “R_(10a),” as used herein, refers to:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or anitro group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, ora C₁-C₆₀ alkoxy group, each unsubstituted or substituted with deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, aC₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂),—B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or anycombination thereof;

a C₃-C₆₀carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxygroup, or a C₆-C₆₀ arylthio group, each unsubstituted or substitutedwith deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₆₀ carbocyclic group, aC₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthiogroup, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof; or

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂),

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ used herein mayeach independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxylgroup; a cyano group; a nitro group; C₁-C₆₀ alkyl group; C₂-C₆₀ alkenylgroup; C₂-C₆₀ alkynyl group; C₁-C₆₀ alkoxy group; or a C₃-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group, each unsubstituted orsubstituted with deuterium, —F, a cyano group, a C₁-C₆₀ alkyl group, aC₁-C₆₀ alkoxy group, a phenyl group, a biphenyl group, or anycombination thereof.

The term “hetero atom,” as used herein, refers to any atom other than acarbon atom. Examples of the heteroatom include O, S, N, P, Si, B, Ge,Se, or any combination thereof.

The term “Ph,” as used herein, refers to a phenyl group, the term “Me,”as used herein, refers to a methyl group, the term “Et,” as used herein,refers to an ethyl group, the term “ter-Bu” or “Bu^(t),” as used herein,refers to a tert-butyl group, and the term “OMe,” as used herein, refersto a methoxy group.

The term “biphenyl group,” as used herein, refers to “a phenyl groupsubstituted with a phenyl group.” In other words, the “biphenyl group”is a substituted phenyl group having a C₆-C₆₀ aryl group as asubstituent.

The term “terphenyl group,” as used herein, refers to “a phenyl groupsubstituted with a biphenyl group.” In other words, the “terphenylgroup” is a substituted phenyl group having, as a substituent, a C₆-C₆₀aryl group substituted with a C₆-C₆₀ aryl group.

* and *′, as used herein, unless defined otherwise, each refer to abinding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and a light-emittingdevice according to embodiments will be described in more detail withreference to Synthesis Examples and Examples. The wording “B was usedinstead of A” used in describing Synthesis Examples refers to that anidentical molar equivalent of B was used in place of A.

EXAMPLES Synthesis Example 1: Synthesis of Compound 46

Synthesis of Intermediate 46-1

1,2-dibromobenzene (2 eq) was dissolved in THF, reacted with nBuLi (2eq) at a temperature of −78° C., and then reacted withdichlorodiphenylsilane (1 eq) to thereby obtain Intermediate 46-1.Intermediate 46-1 was confirmed by LC/MS. (C₂₄H₁₈Br₂Si M+1: 493.21)

Synthesis of Intermediate 46-2

Intermediate 46-1 (1 eq) was dissolved in THF and reacted with nBuLi (1eq) at a temperature of −78° C. At the same time, in another reactionvessel, 1,4-dibromobenzene (1 eq) was dissolved in THF and reacted withnBuLi (1 eq) at a temperature of −78° C. and then reacted withtrichlorophenylsilane (1 eq). The resultant solution was reacted with asolution including Intermediate 46-1 to thereby obtain Intermediate46-2. Intermediate 46-2 was confirmed by LC/MS. (C₃₆H₂₇BrSi₂ M+1:595.12)

Synthesis of Intermediate 46-3

Intermediate 46-2 (1 eq) was dissolved in toluene, and then Pd(PPh₃)Cl₂(0.05 eq), KOAc (3.5 eq), and B₂pin₂ (1.2 eq) were added dropwisethereto and stirred at a temperature of 120° C. for 12 hours to therebyobtain Intermediate 46-3. Intermediate 46-3 was confirmed by LC/MS.(C₄₂H₃₉BO₂Si₂ M+1: 644.27)

Synthesis of Intermediate 46-4

Intermediate 46-3 (1 eq) was dissolved in THF, and Pd(PPh₃)₄ (0.05 eq),2M K₂CO₃ (2 eq), and 2-bromonitrobenzene (1 eq) were added dropwisethereto and stirred at a temperature of 90° C. for 12 hours to therebyobtain Intermediate 46-4. Intermediate 46-4 was confirmed by LC/MS.(C₄₂H₃₁ NO₂Si₂ M+1: 638.21)

Synthesis of Intermediate 46-5

Intermediate 46-4 (1 eq) was dissolved in o-dichlorobenzene, and PPh₃(2.5 eq) was added dropwise thereto and stirred at a temperature of 180°C. for 12 hours to thereby obtain Intermediate 46-5. Intermediate 46-5was confirmed by LC/MS. (C₄₂H₃₁NSi₂ M+1: 606.30) Synthesis of Compound46

10.3 g of Intermediate 46-5 and 3.1 g of9-([1,1′-biphenyl]-2-yl)-3-bromo-9H-carbazole (CAS #=1428551-28-3) weredissolved in toluene, and 0.28 g of Pd₂dba₃, 0.2 ml of P(tBu)₃, and 3.3g of NaOtBu were added dropwise thereto and reacted therewith at atemperature of 120° C. for 12 hours. After the reaction was completed,the resultant reaction solution was extracted using ethylacetate, thecollected organic layer was dried using magnesium sulfate, and a solventwas evaporated therefrom. The obtained residue was separated andpurified by silica gel column chromatography to thereby obtain 4.4 g(yield: 62%) of Compound 46. Compound 46 was confirmed by LC-MS and¹H-NMR.

Synthesis Example 2: Synthesis of Compound 55

Synthesis of Intermediate 55-1

Diphenylether (1 eq) was dissolved in THF and reacted with nBuLi (1 eq)at a temperature of −78° C. At the same time, in another reactionvessel, 1,4-dibromobenzene (1 eq) was dissolved in THF, reacted withnBuLi (1 eq) at a temperature of −78° C., and reacted withtrichlorophenylsilane(1 eq). The resultant solution was reacted with asolution including diphenyl ether to thereby obtain Intermediate 55-1.Intermediate 55-1 was confirmed by LC/MS. (C₂₄H₁₇BrOSi M+1: 429.03)

Synthesis of Intermediate 55-2

Intermediate 55-1 (1 eq) was dissolved in toluene and Pd(PPh₃)₂Cl₂ (0.05eq), KOAc (3.5 eq), and B₂pin₂ (1.2 eq) were added dropwise thereto andstirred at a temperature of 120° C. for 12 hours to thereby obtainIntermediate 55-2. Intermediate 55-2 was confirmed by LC/MS.(C₃₀H₂₉BO₃Si M+1: 477.21)

Synthesis of Intermediate 55-3

Intermediate 55-2 (1 eq) was dissolved in THF and Pd(PPh₃)₄ (0.05 eq),2M K₂CO₃ (2 eq), and 2-bromonitrobenzene (1 eq) were added dropwisethereto and stirred at a temperature of 90° C. for 12 hours to therebyobtain Intermediate 55-3. Intermediate 55-3 was confirmed by LC/MS.(C₃₀H₂₁NO₃Si M+1: 472.12)

Synthesis of Intermediate 55-4

Intermediate 55-3 was dissolved in o-dichlorobenzene (1 eq), and PPh₃(2.5 eq) was added dropwise thereto and stirred at a temperature of 180°C. for 12 hours to thereby obtain Intermediate 55-4. Intermediate 55-4was confirmed by LC/MS. (C₃₀H₂₁NOSi M+1: 439.14)

Synthesis of Intermediate 55-5

9-([1,1′-biphenyl]-3-yl)-3,6-dibromo-9H-carbazole (CAS #=1221237-88-2)(1 eq), carbazole (1 eq), Pd2dba3 (0.05 eq), P(tBu)₃ (0.1 eq), andNaOtBu (1.5 eq) were dissolved in 30 ml of toluene and stirred at atemperature of 120° C. for 12 hours to thereby obtain Intermediate 55-5.Intermediate 55-5 was confirmed by LC/MS. (C₃₆H₂₃BrN₂ M+1: 563.11)

Synthesis of Compound 55

4.3 g of Intermediate 55-4 and 2.5 g of Intermediate 55-5 were dissolvedin 30 ml of toluene, and 0.16 g of Pd₂dba₃, 0.2 ml of P(tBu)₃, and 1.9 gof NaOtBu were added dropwise thereto and reacted therewith for 12 hoursat a temperature of 120° C. After the reaction was completed, theresultant reaction solution was extracted using ethylacetate, thecollected organic layer was dried using magnesium sulfate and a solventwas evaporated therefrom. The obtained residue was separated andpurified by silica gel column chromatography to thereby obtain 2 g(yield: 49%) of Compound 55. Compound 55 was confirmed by LC-MS and¹H-NMR.

Synthesis Example 3: Synthesis of Compound 85

Synthesis of Intermediate 85-1

Intermediate 85-1 was synthesized in substantially the same manner as inthe synthesis of Intermediate 55-1, except that, instead ofdiphenylether, diphenylsulfane was used. Intermediate 85-1 was confirmedby LC/MS. (C₂₄H₁₇BrSSi M+1: 445.11)

Synthesis of Intermediate 85-2

Intermediate 85-2 was synthesized in substantially the same manner as inthe synthesis of Intermediate 55-2, except that, instead of Intermediate55-1, Intermediate 85-1 was used. Intermediate 85-2 was confirmed byLC/MS. (C₃₀H₂₉BO₂SSi M+1: 493.20)

Synthesis of Intermediate 85-3

Intermediate 85-3 was synthesized in substantially the same manner as inthe synthesis of Intermediate 55-3, except that, instead of Intermediate55-2, Intermediate 85-2 was used. Intermediate 85-3 was confirmed byLC/MS. (C₃₀H₂₁NO₂SSi M+1: 488.21)

Synthesis of Intermediate 85-4

Intermediate 85-4 was synthesized in substantially the same manner as inthe synthesis of Intermediate 55-4, except that, instead of Intermediate55-3, Intermediate 85-3 was used. Intermediate 85-4 was confirmed byLC/MS. (C₃₀H₂₁NSSi M+1: 456.11)

Synthesis of Compound 85

4.1 g of Intermediate 85-4 and 9.2 g of9,9′-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (CAS#=877615-05-9) were dissolved in 30 ml of toluene, and 0.33 g ofPd₂dba₃, 0.2 ml of P(tBu)₃, and 3.9 g of NaOtBu were added dropwisethereto and reacted therewith at a temperature of 120° C. for 12 hours.After the reaction was completed, the resultant reaction solution wasextracted using ethylacetate, the collected organic layer was driedusing magnesium sulfate and a solvent was evaporated therefrom. Theobtained residue was separated and purified by silica gel columnchromatography to thereby obtain 5.2 g (yield: 65%) of Compound 85.Compound 85 was confirmed by LC-MS and ¹H-NMR.

Synthesis Example 4: Synthesis of Compound 94

Synthesis of Intermediate 94-1

Intermediate 46-5 (1 eq) and 1-bromo-2-fluorobenzene (2 eq) weredissolved in DMF, and K₃PO₄ (2.5 eq) was added dropwise thereto. Theresultant solution was reacted at a temperature of 160° C. for 12 hoursto thereby obtain Intermediate 94-1. Intermediate 94-1 was confirmed byLC/MS. (C₄₈H₃₄BrNSi₂ M+1: 760.15)

Synthesis of Intermediate 94-2

Intermediate 94-1 (1 eq) was dissolved in THF, nBuLi (1.2 eq) was slowlyadded dropwise thereto at a temperature of −78° C., and trimethylborate(1.4 eq) was reacted therewith for 1 hour to thereby obtain Intermediate94-2. Intermediate 94-2 was confirmed by LC/MS. (C₄₈H₃₆BNO₂Si₂ M+1:726.19)

Synthesis of Compound 94

10.8 g of Intermediate 94-2 and 4.4 g of9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole (CAS#=1268244-56-9) were dissolved in 60 ml of THF, and 0.6 g of Pd(PPh₃)₄,4.3 g of K₂CO₃, and 15 ml of H₂O were added dropwise thereto and reactedtherewith at a temperature of 120° C. for 12 hours. After the reactionwas completed, the resultant reaction solution was extracted usingethylacetate, the collected organic layer was dried using magnesiumsulfate, and a solvent was evaporated therefrom. The obtained residuewas separated and purified by silica gel column chromatography tothereby obtain 5.4 g (yield: 44%) of Compound 94. Compound 94 wasconfirmed by LC-MS and ¹H-NMR.

Synthesis Example 5: Synthesis of Compound 98

3.5 g of Intermediate 55-4 and 1.4 g of2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (CAS #=864377-31-1) weredissolved in 30 ml of toluene, and 0.13 g of Pd₂dba₃, 0.1 ml of P(tBu)₃,and 1.5 g of NaOtBu were added dropwise thereto and reacted therewith ata temperature of 120° C. for 12 hours. After the reaction was completed,the resultant reaction solution was extracted using ethylacetate, thecollected organic layer was dried using magnesium sulfate, and a solventwas evaporated therefrom. The obtained residue was separated andpurified by silica gel column chromatography to thereby obtain 1.4 g(yield: 51%) of Compound 98. Compound 98 was confirmed by LC-MS and¹H-NMR.

Synthesis Example 6: Synthesis of Compound 104

5.8 g of Intermediate 85-4 and 2.5 g of9-(4-([1,1′-biphenyl]-3-yl)-6-chloro-1,3,5-triazin-2-yl)-9H-carbazole(CAS #=2361416-42-2) were dissolved in toluene, and 0.2 g of Pd₂dba₃,0.1 ml of P(tBu)₃, and 2.5 g of NaOtBu were added dropwise thereto andreacted therewith at a temperature of 120° C. for 12 hours. After thereaction was completed, the resultant reaction solution was extractedusing ethylacetate, the collected organic layer was dried usingmagnesium sulfate, and a solvent was evaporated therefrom. The obtainedresidue was separated and purified by silica gel column chromatographyto thereby obtain 2.6 g (yield: 54%) of Compound 104. Compound 104 wasconfirmed by LC-MS and ¹H-NMR.

Synthesis Example 7: Synthesis of Compound 129

Synthesis of Intermediate 129-1

Intermediate 129-1 was synthesized in substantially the same manner asin the synthesis of Intermediate 94-1, except that, instead ofIntermediate 46-5, Intermediate 55-4 was used. Intermediate 129-1 wasconfirmed by LC/MS. (C₃₆H₂₄BrNOSi M+1: 594.09)

Synthesis of Intermediate 129-2

Intermediate 129-2 was synthesized in substantially the same manner asin the synthesis of Intermediate 94-2, except that, instead ofIntermediate 94-1, Intermediate 129-1 was used. Intermediate 129-2 wasconfirmed by LC/MS. (C₃₆H₂₆BNO₃Si M+1: 560.19) Synthesis of Compound 129

1.8 g of Intermediate 129-2 was dissolved in 40 ml of THF, and 0.12 g ofPd(PPh₃)₄, 0.9 g of K₂CO₃, and 1.2 g of9,9′-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole)(CAS#=877615-05-9) were added dropwise thereto and stirred at a temperatureof 90° C. for 12 hours. After the reaction was completed, the resultantreaction solution was extracted using ethylacetate, the collectedorganic layer was dried using magnesium sulfate, and a solvent wasevaporated therefrom. The obtained residue was separated and purified bysilica gel column chromatography to thereby obtain 1.8 g (yield: 73%) ofCompound 129. Compound 129 was confirmed by LC-MS and ¹H-NMR.

Table 1 shows ¹H NMR and LC-MS of the synthesized compounds. Synthesismethods for other compounds than the compounds shown in Table 1 may beeasily recognized by those skilled in the technical field by referringto the synthesis paths and source materials described above.

TABLE 1 LC-MS Compound ¹H NMR (CDCI₃, 400 MHz) found calc. 468.55-8.53(d, 2H), 8.19(d, 1H), 7.94- 923.21 922.32 7.91 (m, 3H), 7.80(t,1H), 7.72- 7.67(m, 3H), 7.58-7.19(m, 36H) 55 8.55-8.53(m, 2H),8.21-8.19(m, 3H), 922.31 921.32 8.08(d, 1H), 7.94(d, 1H), 7.75- 7.09(m,33H) 85 8.55-8.53(m, 3H), 8.19(d, 3H), 7.94(d, 865.23 864.25 2H),7.68(d, 1H), 7.58-7.11 (m, 27H) 94 8.55-8.53(d, 2H), 8.36(d, 2H),8.19(d, 1002.29 1001.34 2H), 7.94-7.91 (d, 3H), 7.80(t, 1H), 7.68(s,1H), 7.56-7.16(m, 36H) 98 8.53(d, 1H), 8.36(d, 4H), 8.24-8.19(m, 747.23746.25 3H), 7.68-7.38(m, 20H), 7.28-7.20(m, 2H), 7.10-7.09(m, 4H) 1048.55-8.53(d, 2H), 8.38(d, 1H), 8.19(d, 852.25 851.25 1H), 7.94(m, 2H),7.75-7.68(m, 4H), 7.58-7.16(m, 27H) 129 8.55-8.53(m, 3H), 8.19(d, 3H),7.94- 925.29 924.30 7.91 (d, 4H), 7.80(t, 1H), 7.68(s, 1H), 7.58-7.10(m,28H)

Example 1

As an anode, a Corning 15 Ω/cm² (1,200 Å) ITO glass substrate was cut toa size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and purewater each for 5 minutes, and then cleaned by exposure to ultravioletrays and ozone for 30 minutes. The ITO glass substrate was loaded onto avacuum deposition apparatus.

NPB was vacuum-deposited on the ITO anode formed on the ITO glasssubstrate to form a hole injection layer having a thickness of 300 Å,and then, mCP was vacuum-deposited on the hole injection layer to form ahole transport layer having a thickness of 200 Å.

Compound 46 (host) and Ir(pmp)₃(dopant) were co-deposited at a weightratio of 92:8 on the hole transport layer to form an emission layerhaving a thickness of 250 Å.

Next, TAZ was deposited on the emission layer to form an electrontransport layer having a thickness of 200 Å, LiF was deposited on theelectron transport layer to form an electron injection layer having athickness of 10 Å, and Al was vacuum-deposited on the electron injectionlayer to form an LiF/Al electrode having a thickness of 100 Å, therebycompleting the manufacture of a light-emitting device.

Examples 2 to 7 and Comparative Examples 1 to 3

Light-emitting devices were manufactured in substantially the samemanner as in Example 1, except that, in forming the emission layer, thecompounds shown in Table 2 were each used instead of Compound 46.

Evaluation Example 1

To evaluate characteristics of the light-emitting devices manufacturedaccording to Examples 1 to 7 and Comparative Examples 1 to 3, thedriving voltage at the current density of 10 mA/cm², luminescenceefficiency, and maximum external quantum efficiency (EQE) thereof weremeasured. The driving voltage of an light-emitting device were measuredusing a source meter (Keithley Instrument Inc., 2400 series), and themaximum external quantum efficiency was measured using the externalquantum efficiency measurement apparatus C9920-2-12 of HamamatsuPhotonics Inc. In evaluating the maximum external quantum efficiency,the luminance/current density was measured using a luminance meter thatwas calibrated for wavelength sensitivity, and the maximum externalquantum efficiency was converted by assuming an angular luminancedistribution (Lambertian) which introduced a perfect reflectingdiffuser. Table 2 below shows the evaluation results of thecharacteristics of the light-emitting devices.

TABLE 2 Maximum Lumines- external Host of Driving cence quantum emissionvoltage Efficiency efficiency Emission layer (V) (cd/A) (%) colorExample 1 Compound 4.8 18.5 28.4 Blue 46 Example 2 Compound 4.5 17.928.0 Blue 55 Example 3 Compound 4.2 18.4 28.7 Blue 85 Example 4 Compound4.4 18.9 28.6 Blue 94 Example 5 Compound 4.6 18.7 28.5 Blue 98 Example 6Compound 4.7 18.3 28.3 Blue 104 Example 7 Compound 4.4 18.5 28.9 Blue129 Comparative Compound 5.3 14.3 24.4 Blue Example 1 A ComparativeCompound 5.9 14.6 23.1 Blue Example 2 B Comparative Compound 5.1 14.224.3 Blue Example 3 C

From Table 2, it can be seen that the light-emitting devices of Examples1 to 7 have lower driving voltage, excellent luminescence efficiency,and maximum quantum efficiency compared to the light-emitting devices ofComparative Examples 1 to 3.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments. While one or more embodiments have beendescribed with reference to the figures, it will be understood by thoseof ordinary skill in the art that various changes in form and detailsmay be made therein without departing from the spirit and scope of thepresent disclosure as defined by the following claims, and equivalentsthereof.

What is claimed is:
 1. A light-emitting device comprising: a firstelectrode; a second electrode facing the first electrode; an interlayerbetween the first electrode and the second electrode and comprising anemission layer; and at least one heterocyclic compound represented byFormula 1:

wherein, in Formula 1, X₁ is O, S, or Si(R₁₁)(R₁₂), Ar is a C₅-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group, A₁ is a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R₁₀ ora C₁-C₆₀ heterocyclic group unsubstituted or substituted with at leastone R₁₀, L₁ is a single bond, a C₅-C₆₀ carbocyclic group unsubstitutedor substituted with at least one R_(10a), or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a), n1 is an integerselected from 1 to 3, R₁ to R₃, R₁₀, R₁₁, and R₁₂ are each independentlyhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, a C₁-C₆₀ alkyl group unsubstituted or substituted with atleast one R_(10a), a C₂-C₆₀ alkenyl group unsubstituted or substitutedwith at least one R_(10a), a C₂-C₆₀ alkynyl group unsubstituted orsubstituted with at least one R_(10a), a C₁-C₆₀ alkoxy groupunsubstituted or substituted with at least one R_(10a), a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least oneR_(10a), a C₁-C₆₀ heterocyclic group unsubstituted or substituted withat least one R_(10a), a C₆-C₆₀ aryloxy group unsubstituted orsubstituted with at least one R_(10a), a C₆-C₆₀ arylthio groupunsubstituted or substituted with at least one R_(10a), —Si(Q₁)(Q₂)(Q₃),—N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂), d1is an integer selected from 1 to 8, d2 is an integer selected from 1 to10, d3 is an integer selected from 1 to 7, and R_(10a) is: deuterium(-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, an amidinogroup, a hydrazino group, a hydrazono group, or a nitro group; a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxy group,a C₆-C₆₀ arylthio group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂),—C(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or any combination thereof;a C₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀aryloxy group, or a C₆-C₆₀ arylthio group, each unsubstituted orsubstituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₆₀ carbocyclic group,a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthiogroup, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof; or—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or —P(Q₃₁)(Q₃₂), wherein Q₁ to Q₃, Q₁₁to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are each independently: hydrogen;deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitrogroup; a C₁-C₆₀ alkyl group; a C₂-C₆₀ alkenyl group; a C₂-C₆₀ alkynylgroup; a C₁-C₆₀ alkoxy group; or a C₃-C₆₀ carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium,—F, a cyano group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a phenylgroup, a biphenyl group, or any combination thereof.
 2. Thelight-emitting device of claim 1, wherein the first electrode is ananode, the second electrode is a cathode, the interlayer furthercomprises a hole transport region between the first electrode and theemission layer and an electron transport region between the emissionlayer and the second electrode, the hole transport region comprises ahole injection layer, a hole transport layer, an emission auxiliarylayer, an electron blocking layer, or any combination thereof, and theelectron transport region further comprises a buffer layer, a holeblocking layer, an electron control layer, an electron transport layer,an electron injection layer, or any combination thereof.
 3. Thelight-emitting device of claim 1, wherein the emission layer comprisesthe at least one heterocyclic compound.
 4. The light-emitting device ofclaim 1, wherein the emission layer comprises a host and a dopant, thehost and the dopant are different from each other, an amount of the hostis greater than an amount of the dopant, and the host comprises the atleast one heterocyclic compound.
 5. The light-emitting device of claim4, wherein the dopant comprises a transition metal.
 6. Thelight-emitting device of claim 3, wherein the emission layer emits bluelight or blue-green light.
 7. An electronic apparatus comprising: thelight-emitting device of claim 1; and a thin-film transistor, whereinthe thin-film transistor comprises a source electrode and a drainelectrode, and the first electrode of the light-emitting device iselectrically coupled to the source electrode or the drain electrode. 8.The electronic apparatus of claim 7, further comprising a color filter,a color conversion layer, a touch screen layer, a polarizing layer, orany combination thereof.
 9. A heterocyclic compound represented byFormula 1:

wherein, in Formula 1, X₁ is O, S, or Si(R₁₁)(R₁₂), Ar is a C₅-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group, A₁ is a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R₁₀ ora C₁-C₆₀ heterocyclic group unsubstituted or substituted with at leastone R₁₀, L₁ is a single bond, a C₅-C₆₀ carbocyclic group unsubstitutedor substituted with at least one R_(10a), or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a), n1 is an integerselected from 1 to 3, R₁ to R₃, R₁₀, R₁₁, and R₁₂ are each independentlyhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, a C₁-C₆₀ alkyl group unsubstituted or substituted with atleast one R_(10a), a C₂-C₆₀ alkenyl group unsubstituted or substitutedwith at least one R_(10a), a C₂-C₆₀ alkynyl group unsubstituted orsubstituted with at least one R_(10a), a C₁-C₆₀ alkoxy groupunsubstituted or substituted with at least one R_(10a), a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least oneR_(10a), a C₁-C₆₀ heterocyclic group unsubstituted or substituted withat least one R_(10a), a C₆-C₆₀ aryloxy group unsubstituted orsubstituted with at least one R_(10a), a C₆-C₆₀ arylthio groupunsubstituted or substituted with at least one R_(10a), —Si(Q₁)(Q₂)(Q₃),—N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂), d1is an integer selected from 1 to 8, d2 is an integer selected from 1 to10, d3 is an integer selected from 1 to 7, and R_(10a) is: deuterium(-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, an amidinogroup, a hydrazino group, a hydrazono group, or a nitro group; a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxy group,a C₆-C₆₀ arylthio group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂),—C(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or any combination thereof;a C₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀aryloxy group, or a C₆-C₆₀ arylthio group, each unsubstituted orsubstituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₆₀ carbocyclic group,a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthiogroup, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof; or—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or —P(Q₃₁)(Q₃₂), wherein Q₁ to Q₃, Q₁₁to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are each independently: hydrogen;deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitrogroup; a C₁-C₆₀ alkyl group; a C₂-C₆₀ alkenyl group; a C₂-C₆₀ alkynylgroup; a C₁-C₆₀ alkoxy group; or a C₃-C₆₀ carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium,—F, a cyano group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a phenylgroup, a biphenyl group, or any combination thereof.
 10. Theheterocyclic compound of claim 9, wherein Ar is a benzene group, anaphthalene group, an anthracene group, a phenanthrene group, atriphenylene group, a pyrene group, a chrysene group, a cyclopentadienegroup, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furangroup, an indole group, a benzoborole group, a benzophosphole group, anindene group, a benzosilole group, a benzogermole group, abenzothiophene group, a benzoselenophene group, a benzofuran group, acarbazole group, a dibenzoborole group, a dibenzophosphole group, afluorene group, a dibenzosilole group, a dibenzogermole group, adibenzothiophene group, a dibenzoselenophene group, a dibenzofurangroup, a dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, adibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a pyrrole group, a pyrazolegroup, an imidazole group, a triazole group, an oxazole group, anisooxazole group, a thiazole group, an isothiazole group, an oxadiazolegroup, a thiadiazole group, a benzopyrazole group, a benzimidazolegroup, a benzoxazole group, a benzothiazole group, a benzoxadiazolegroup, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group,or a 5,6,7,8-tetrahydroquinoline group.
 11. The heterocyclic compound ofclaim 9, wherein A₁ is a π electron-rich C₃-C₆₀ cyclic groupunsubstituted or substituted with at least one R₁₀ or a πelectron-deficient nitrogen-containing C₁-C₆₀ cyclic group unsubstitutedor substituted with at least one R₁₀, and R₁₀ is as defined in claim 9.12. The heterocyclic compound of claim 9, wherein A₁ is a benzene group,a naphthalene group, an anthracene group, a phenanthrene group, atriphenylene group, a pyrene group, a chrysene group, a cyclopentadienegroup, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furangroup, an indole group, a benzoborole group, a benzophosphole group, anindene group, a benzosilole group, a benzogermole group, abenzothiophene group, a benzoselenophene group, a benzofuran group, acarbazole group, a dibenzoborole group, a dibenzophosphole group, afluorene group, a dibenzosilole group, a dibenzogermole group, adibenzothiophene group, a dibenzoselenophene group, a dibenzofurangroup, a dibenzothiophene 5-oxide group, a 9H-a fluorene-9-one group, adibenzothiophene 5,5-dioxide group, an azaindole group, anazabenzoborole group, an azabenzophosphole group, an azaindene group, anazabenzosilole group, an azabenzogermole group, an azabenzothiophenegroup, an azabenzoselenophene group, an azabenzofuran group, anazacarbazole group, an azadibenzoborole group, an azadibenzophospholegroup, an azafluorene group, an azadibenzosilole group, anazadibenzogermole group, an azadibenzothiophene group, anazadibenzoselenophene group, an azadibenzofuran group, anazadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, anazadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a pyrrole group, a pyrazolegroup, an imidazole group, a triazole group, an oxazole group, anisooxazole group, a thiazole group, an isothiazole group, an oxadiazolegroup, a thiadiazole group, a benzopyrazole group, a benzimidazolegroup, a benzoxazole group, a benzothiazole group, a benzoxadiazolegroup, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group,or a 5,6,7,8-tetrahydroquinoline group, each unsubstituted orsubstituted with at least one R₁₀, and R₁₀ is as defined in claim
 9. 13.The heterocyclic compound of claim 9, wherein A₁ is a group representedby Formula 2 or Formula 3:

wherein, in Formulae 2 and 3, Y₁ is N or C(R_(1a)), Y₂ is N orC(R_(2a)), Y₃ is N or C(R_(3a)), L₂₁, L₂₂, and L₃₁ are eachindependently a single bond, a C₅-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R_(10a), or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a), n21, n22, andn31 are each independently an integer selected from 1 to 3, * indicatesa binding site to a neighboring atom, R_(1a) to R_(3a), R₂₁, R₂₂, R₃₁,and R₃₂ are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl groupunsubstituted or substituted with at least one R_(10a), a C₂-C₆₀ alkenylgroup unsubstituted or substituted with at least one R_(10a), a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_(10a), aC₁-C₆₀ alkoxy group unsubstituted or substituted with at least oneR_(10a), a C₃-C₆₀ carbocyclic group unsubstituted or substituted with atleast one R_(10a), a C₁-C₆₀ heterocyclic group unsubstituted orsubstituted with at least one R_(10a), a C₆-C₆₀ aryloxy groupunsubstituted or substituted with at least one R_(10a), a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_(10a),—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or—P(═O)(Q₁)(Q₂), d21, d22, and d31 are each independently an integerselected from 1 to 10, d32 is an integer selected from 1 to 7, andR_(10a) is as defined in claim
 9. 14. The heterocyclic compound of claim13, wherein L₁, L₂₁, L₂₂, and L₃₁ are each independently: a single bond;or a benzene group, a naphthalene group, an anthracene group, aphenanthrene group, a triphenylene group, a pyrene group, a chrysenegroup, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, athiophene group, a furan group, an indole group, a benzoborole group, abenzophosphole group, an indene group, a benzosilole group, abenzogermole group, a benzothiophene group, a benzoselenophene group, abenzofuran group, a carbazole group, a dibenzoborole group, adibenzophosphole group, a fluorene group, a dibenzosilole group, adibenzogermole group, a dibenzothiophene group, a dibenzoselenophenegroup, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-afluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindolegroup, an azabenzoborole group, an azabenzophosphole group, an azaindenegroup, an azabenzosilole group, an azabenzogermole group, anazabenzothiophene group, an azabenzoselenophene group, an azabenzofurangroup, an azacarbazole group, an azadibenzoborole group, anazadibenzophosphole group, an azafluorene group, an azadibenzosilolegroup, an azadibenzogermole group, an azadibenzothiophene group, anazadibenzoselenophene group, an azadibenzofuran group, anazadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, anazadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a pyrrole group, a pyrazolegroup, an imidazole group, a triazole group, an oxazole group, anisooxazole group, a thiazole group, an isothiazole group, an oxadiazolegroup, a thiadiazole group, a benzopyrazole group, a benzimidazolegroup, a benzoxazole group, a benzothiazole group, a benzoxadiazolegroup, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group,or a 5,6,7,8-tetrahydroquinoline group, each unsubstituted orsubstituted with at least one R_(10a), and R_(10a) is as defined inclaim
 13. 15. The heterocyclic compound of claim 13, wherein L₁, L₂₁,L₂₂, and L₃₁ are each independently a single bond or selected fromFormulae 10-1 to 10-40:

wherein, in Formulae 10-1 to 10-40, Y₁ is O or S, Y₂ is O, S, N(Z₃), orC(Z₃)(Z₄), Z₁ to Z₄ are each the same as described in connection with R₁in claim 9, e4 is an integer selected from 1 to 4, e6 is an integerselected from 1 to 6, e7 is an integer selected from 1 to 7, e8 is aninteger selected from 1 to 8, and * and *′ each indicate a binding siteto a neighboring atom.
 16. The heterocyclic compound of claim 9, whereinFormula 1 is represented by Formula 1-1:

wherein, in Formula 1-1, X₁, A₁, L₁, n1, R₁ to R₃, d1, and d3 are asdefined in claim 9, and d2 is an integer selected from 1 to
 5. 17. Theheterocyclic compound of claim 9, wherein Formula 1 is represented byone of Formulae 1-11 to 1-14:

wherein, in Formulae 1-11 to 1-14, X₁, Ar, L₁, n1, A₁, R₁ to R₃, and d1to d3 are as defined in claim
 9. 18. The heterocyclic compound of claim13, wherein Formula 3 is represented by one of Formulae 3-1 to 3-4:

wherein, in Formulae 3-1 to 3-4, L₃₁, n31, R₃₁, R₃₂, d31, and d32 are asdefined in claim
 13. 19. The heterocyclic compound of claim 13, whereinR₁ to R₃, R₁₀ to R₁₂, R_(1a) to R_(3a), R₂₁, R₂₂, R₃₁, and R₃₂ are eachindependently selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, and a C₁-C₂₀alkoxy group; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, eachsubstituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD₃,—CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a biphenyl group, a C₁-C₁₀ alkylphenyl group, a naphthylgroup, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azafluorenyl group, and anazadibenzosilolyl group, each unsubstituted or substituted with at leastone of deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group,a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cycloctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, an azacarbazolyl group, anazadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenylgroup, an azadibenzosilolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —P(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and—P(═O)(Q₃₁)(Q₃₂); and —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), wherein Q₁ to Q₃ and Q₃₁ toQ₃₃ are each independently selected from —CH₃, —CD₃, —CD₂H, —CDH₂,—CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂,—CHDCD₃, —CD₂CD₃, —CD₂CD₂H, and —CD₂CDH₂; and an n-propyl group, aniso-propyl group, an n-butyl group, an isobutyl group, a sec-butylgroup, a tert-butyl group, an n-pentyl group, an isopentyl group, asec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group,a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinylgroup, and a triazinyl group, each unsubstituted or substituted with atleast one selected from deuterium, a C₁-C₁₀ alkyl group, a phenyl group,a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinylgroup, a pyrazinyl group, and a triazinyl group.
 20. The heterocycliccompound of claim 9, wherein the heterocyclic compound is one ofCompounds 1 to 130: